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 Parouse.com



HU-210
HU-210
is a synthetic cannabinoid that was first synthesized in 1988 from (1R,5S)-myrtenol[1] by a group led by Professor Raphael Mechoulam at the Hebrew University.[2][3][4] HU-210
HU-210
is 100 to 800 times more potent than natural THC
THC
from cannabis and has an extended duration of action.[5] HU-210
HU-210
is the (–)-1,1-dimethylheptyl analog of 11-hydroxy- Δ8- tetrahydrocannabinol; in some references it is called 1,1-dimethylheptyl- 11-hydroxytetrahydrocannabinol. The abbreviation "HU" stands for Hebrew University.

Contents

1 Effects and research 2 Chemistry 3 Recreational use 4 Legal status

4.1 New Zealand 4.2 United States

4.2.1 Alabama 4.2.2 Florida 4.2.3 Vermont

5 Other HU Cannabinoids 6 See also 7 References 8 External links

Effects and research[edit] The (+) enantiomer of HU-210
HU-210
has almost all of the cannabinoid activity, with the (−) enantiomer HU-211
HU-211
being inactive as a cannabinoid but instead acting as an NMDA antagonist
NMDA antagonist
having neuroprotective effects.[6][7] HU-210
HU-210
promotes proliferation, but not differentiation, of cultured embryonic hippocampal neural stem and progenitor cells likely via a sequential activation of CB1 receptors, Gi/o proteins, and ERK signaling. It was also indicated by this increased neural growth to entail antianxiety and antidepressant effects.[8] HU-210, alongside other synthetic cannabinoids like WIN 55,212-2
WIN 55,212-2
and JWH-133, is implicated in preventing the inflammation caused by amyloid beta proteins involved in Alzheimer's disease, in addition to preventing cognitive impairment and loss of neuronal markers. This anti-inflammatory action is induced through the activation of cannabinoid receptors, which prevents microglial activation that elicits the inflammation. In addition, cannabinoids completely abolish neurotoxicity related to microglia activation in rat models.[9] HU-210
HU-210
is a potent analgesic with many of the same effects as natural THC. Chemistry[edit] HU-210
HU-210
is the enantiomer of HU-211
HU-211
(Dexanabinol). The original synthesis of HU-210
HU-210
is based on an acid-catalyzed condensation of (–)- Myrtenol
Myrtenol
and 1,1-Dimethylheptylresorcinol (3,5-Dihydroxy-1-(1,1-dimethylheptyl)benzol).[10]

Recreational use[edit] According to the U.S. Customs and Border Protection, HU-210
HU-210
was discovered in Spice Gold incense products seized at the US border in January 2009. Over 100 pounds (45 kg) of Spice products were seized based on this finding.[11] HU-210
HU-210
was also detected in three Spice products in the UK, as reported in June 2009.[12] Legal status[edit] HU-210
HU-210
is not listed in the schedules set out by the United Nations' Single Convention on Narcotic Drugs
Single Convention on Narcotic Drugs
from 1961 nor their Convention on Psychotropic Substances from 1971,[13] so the signatory countries to these international drug control treaties are not required by said treaties to control HU-210. New Zealand[edit] HU-210
HU-210
is banned in New Zealand as of 8 May 2014.[14] United States[edit] HU-210
HU-210
is not listed in the list of scheduled controlled substances in the USA.[15] It is therefore not scheduled at the federal level in the United States, but it is possible that HU-210
HU-210
could legally be considered an analog of Delta-8- THC
THC
(which is one of the substances controlled in Schedule I as "tetrahydrocannabinols"), and therefore sales or possession could potentially be prosecuted under the Federal Analogue Act.[16] A brief profile of HU-210
HU-210
written and published by the Drug Enforcement Administration
Drug Enforcement Administration
(DEA) in 2009 (but subsequently removed from the DEA's website several years later) stated that HU-210 is a Schedule I controlled substance under the Controlled Substances Act due to being similar to THC.[17] This indicates that the DEA might legally consider HU-210
HU-210
to be an analogue of Delta-8- THC
THC
for the purposes of applying the Federal Analog Act to those that handle HU-210. An elucidation of the rationale for the DEA's claim was not presented, no references were cited, and the claim was eventually removed from the DEA's website. A version of the document (updated in 2013), now in PDF
PDF
form, exists on the DEA Office of Diversion Control's website.[18] Claimed in this possibly misleading though definitive sounding document, with the same lack of detailed explanation or citation, is:

HU-210
HU-210
is a schedule I controlled substance under the CSA. ”

Alabama[edit] HU-210
HU-210
is a Schedule I controlled substance in Alabama.[19]

(4)a. A synthetic controlled substance that is any material, mixture, or preparation that contains any quantity of the following chemical compounds, their salts, isomers and salts of isomers, unless specifically excepted, whenever the existence of these salts, isomers and salts of isomers is possible within the specific chemical designation or compound: ... 9. (6aR, 10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol, some trade or other names: HU-210.

Florida[edit] HU-210
HU-210
is a Schedule I controlled substance, categorized as a hallucinogen, making it illegal to buy, sell, or possess in the state of Florida
Florida
without a license.[20]

“ (c) Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation that contains any quantity of the following hallucinogenic substances or that contains any of their salts, isomers, including optical, positional, or geometric isomers, homologues, nitrogen-heterocyclic analogs, esters, ethers, and salts of isomers, homologues, nitrogen-heterocyclic analogs, esters, or ethers, if the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation or class description: ... 47. HU-210 [(6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol].

Vermont[edit] Effective January 1, 2016, HU-210
HU-210
is a regulated drug in Vermont designated as a "Hallucinogenic Drug."[21]

“Hallucinogenic Drug” means those specified in Section 7 of this rule including stramonium, mescaline or peyote, lysergic acid diethylamide, and psilocybin, and all synthetic equivalents of chemicals contained in resinous extractives of Cannabis sativa, or any salts or derivatives or compounds of any preparations or mixtures thereof, and any other substance having a hallucinogenic effect in the regulations adopted by the Board of Health under 18 V.S.A.§ 4202. ... • Cannabimimetic Agents means, collectively, any chemical that is a cannabinoid receptor type 1 (CB1) or cannabinoid receptor type 2 (CB2) agonist, or any salts, isomers, derivatives, or analogs of these chemicals. Structural classes include but are not limited to: (a) 2-(3-hydroxycyclohexyl)phenol with substitution at the 5-position of the phenolic ring by alkyl or alkenyl, whether or not substituted on the cyclohexyl ring to any extent. (b) 3-(1-naphthoyl)indole or 3-(1-naphthyl)indole with substitution at the nitrogen atom of the indole ring, whether or not further substituted on the indole ring to any extent, whether or not substituted on the naphthoyl or naphthyl ring to any extent. (c) 3-(1-naphthoyl)pyrrole with substitution at the nitrogen atom of the pyrrole ring, whether or not further substituted in the pyrrole ring to any extent, whether or not substituted on the naphthoyl ring to any extent. (d) 1-(1-naphthylmethyl)indene with substitution of the 3-position of the indene ring, whether or not further substituted in the indene ring to any extent, whether or not substituted on the naphthyl ring to any extent. (e) 3-phenylacetylindole or 3-benzoylindole with substitution at the nitrogen atom of the indole ring, whether or not further substituted in the indole ring to any extent, whether or not substituted on the phenyl ring to any extent. (f) indole- (2,2,3,3-tetramethylcyclopropyl)methanone, with substitution at the nitrogen atom of the indole ring, whether or not further substituted in the indole ring to any extent, whether or not substituted on the phenyl ring to any extent. (g) N- adamantyl-indole-3-carboxamide, with substitution at the nitrogen atom of the indole ring, whether or not further substituted in the indole ring to any extent, whether or not substituted on the phenyl ring to any extent. (h) (1,3-thiazol-2- ylidine)-2,2,3,3- tetramethylcyclopropane-1-carboxamide, with substitution to any extent at any position of the thiazolylidine ring. ... • HU-210; (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3- (2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c] chromen-1-ol; OR [(6aR,10aR)-9-(hy droxymethyl)- 6,6-dimethyl-3-(2-methyl octan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol; OR 1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol

Other HU Cannabinoids[edit]

HU-211 HU-239 HU-243 HU-308 HU-320 HU-331 HU-336 HU-345

See also[edit]

Delta-8-THC CP 47,497 JWH-018 Cannabinoids

References[edit]

^ Mechoulam, R., Lander, N., Breuer, A., Zahalka, J. Synthesis of the Individual, Pharmacologically Distinct, Enantiomers of a Tetrahydrocannabinol
Tetrahydrocannabinol
Derivative. Tetrahedron: Asymmetry. 1990. Vol 1, No 5. pp 315-318. ^ Mechoulam, R.; et al. (1988). "Enantiomeric cannabinoids: stereospecificity of psychotropic activity". Experientia. 44 (9): 762–764. doi:10.1007/BF01959156. PMID 3416993.  ^ Little PJ, Compton DR, Mechoulam R, Martin BR (Mar 1989). "Stereochemical effects of 11-OH-Δ8-THC-dimethylheptyl in mice and dogs". Pharmacology Biochemistry and Behavior. 32 (3): 661–666. doi:10.1016/0091-3057(89)90014-2.  ^ Järbe, T.; Hiltunen, A.; Mechoulam, R. (1989). "Stereospecificity of the discriminative stimulus functions of the dimethylheptyl homologs of 11-hydroxy-delta 8-tetrahydrocannabinol in rats and pigeons". The Journal of Pharmacology and Experimental Therapeutics. 250 (3): 1000–1005. PMID 2550611.  ^ Devane, W. A.; et al. (1992). "A novel probe for the cannabinoid receptor". Journal of Medicinal Chemistry. 35 (11): 2065–2069. doi:10.1021/jm00089a018. PMID 1317925.  ^ Howlett, A.; Champion, T.; Wilken, G.; Mechoulam, R. (1990). "Stereochemical effects of 11-OH-Δ8-tetrahydrocannabinol-dimethylheptyl to inhibit adenylate cyclase and bind to the cannabinoid receptor". Neuropharmacology. 29 (2): 161–5. doi:10.1016/0028-3908(90)90056-W. PMID 2158635.  ^ Darlington CL (October 2003). "Dexanabinol: a novel cannabinoid with neuroprotective properties". IDrugs : the Investigational Drugs Journal. 6 (10): 976–9. PMID 14534855.  ^ Jiang, W.; et al. (2005). " Cannabinoids
Cannabinoids
promote embryonic and adult hippocampus neurogenesis and produce anxiolytic- and antidepressant-like effects". The Journal of Clinical Investigation. 115 (11): 3104–3116. doi:10.1172/JCI25509. PMC 1253627 . PMID 16224541.  ^ Ramírez Bg, E. A. ; Blázquez, C.; Gómez Del Pulgar, T.; Guzmán, M.; De Ceballos, M. L. (2005). "Prevention of Alzheimer's disease pathology by cannabinoids: neuroprotection mediated by blockade of microglial activation". Journal of Neuroscience. 25 (8): 1904–1913. doi:10.1523/JNEUROSCI.4540-04.2005. PMID 15728830.  ^ R. Mechoulam, N. Lander, A. Breuer, J. Zahalka: In Synthesis of the Individual, Pharmacologically Distinct, Enantiomers of a Tetrahydrocannabinol
Tetrahydrocannabinol
Derivative. Tetrahedron: Asymmetry 1990, 5, 315-318. ^ "Lab Results Confirm CBP in Ohio Discover Synthetic Narcotics in Incense Packets - CBP.gov". [permanent dead link] ^ "EMCDDA Action on new drugs briefing paper: Understanding the 'Spice' phenomenon" (PDF).  ^ UN International Drug Control Conventions ^ https://www.drugfoundation.org.nz/synthetic-cannabinoids/what-they-are ^ §1308.11 Schedule I. ^ Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary ^ "Spice Cannabinoid
Cannabinoid
- HU-210". Archived from the original on 2012-01-17.  ^ HU-210 [(6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c] chromen-1-ol)] [Purported Ingredient of “Spice”] (PDF). DEA Office of Diversion Control. Web. January 2013. ^ " Alabama
Alabama
Senate Bill 333 - Controlled substances, Schedule I, additional synthetic controlled substances and analogue substances included in, trafficking in controlled substance analogues, requisite weight increased, Secs. 13A-12-231, 20-2-23 am'd". March 2014. Retrieved 2 February 2017.  ^ Florida
Florida
Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL ^ Vermont DOH - Regulated Drug Rule 2016 .PDF

External links[edit]

Comment in Nature on the article about neurogenesis.

v t e

Cannabinoids

Phytocannabinoids

Alkylamides Caryophyllene CBC CBCV CBD CBDV CBG CBGM CBGV CBL CBDL CBN CBV Epigallocatechin gallate Gallocatechol Perrottetinene Serinolamide A THC THC-C4 THCA THCV Yangonin

Active metabolites: 8,11-DiOH-THC 11-COOH-THC 11-OH-THC

Endocannabinoids

Arachidonoyl ethanolamide (AEA; anandamide) 2-Arachidonoylglycerol
2-Arachidonoylglycerol
(2-AG) 2-Arachidonyl glyceryl ether
2-Arachidonyl glyceryl ether
(2-AGE; noladin ether) 2-Oleoylglycerol
2-Oleoylglycerol
(2-OG) N-Arachidonoyl dopamine
N-Arachidonoyl dopamine
(NADA) N-Arachidonylglycine
N-Arachidonylglycine
(NAGly) 2-Arachidonoyl lysophosphatidylinositol (2-ALPI) N- Arachidonoyl serotonin
Arachidonoyl serotonin
(AA-5-HT) Docosatetraenoylethanolamide
Docosatetraenoylethanolamide
(DEA) Lysophosphatidylinositol
Lysophosphatidylinositol
(LPI) Oleamide Oleoylethanolamide
Oleoylethanolamide
(OEA) Palmitoylethanolamide
Palmitoylethanolamide
(PEA) RVD-Hpα Stearoylethanolamide (SEA) O-Arachidonoyl ethanolamine (O-AEA; virodhamine)

Synthetic cannabinoids

Classical cannabinoids (dibenzopyrans)

A-40174 A-41988 A-42574 Ajulemic acid AM-087 AM-411 AM-855 AM-905 AM-906 AM-919 AM-926 AM-938 AM-2389 AM-4030 AMG-1 AMG-3 AMG-36 AMG-41 Dexanabinol
Dexanabinol
(HU-211) DMHP Dronabinol HHC HU-210 HU-243 JWH-051 JWH-133 JWH-139 JWH-161 JWH-229 JWH-359 KM-233 L-759,633 L-759,656 Levonantradol
Levonantradol
(CP 50,5561) Menabitan Nabazenil Nabidrox (Canbisol) Nabilone Nabitan Naboctate O-224 O-581 O-774 O-806 O-823 O-1057 O-1125 O-1191 O-1238 O-2048 O-2113 O-2365 O-2372 O-2373 O-2383 O-2426 O-2484 O-2545 O-2694 O-2715 O-2716 O-3223 O-3226 Parahexyl Pirnabine THC-O-acetate THC-O-phosphate

Non-classical cannabinoids

Cannabicyclohexanol CBD-DMH CP 47,497 (C6)-CP 47,497 (C9)-CP 47,497 CP 55,244 CP 55,940 HU-308 HU-320 HU-331 HU-336 HU-345 HU-446 HU-465 HU-910 HUF-101 Nonabine O-1376 O-1422 O-1601 O-1656 O-1657 O-1660 O-1663 O-1871 SPA-229 Tinabinol

Benzoylindoles

1-Butyl-3-(2-methoxybenzoyl)indole 1-Butyl-3-(4-methoxybenzoyl)indole 1-Pentyl-3-(2-methoxybenzoyl)indole AM-630 AM-679 AM-694 AM-1241 AM-2233 GW-405,833
GW-405,833
(L-768,242) Pravadoline RCS-4 WIN 54,461

Naphthoylindoles

AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 CHM-081 EAM-2201 FUB-JWH-018 JWH-007 JWH-015 JWH-018 JWH-019 JWH-073 JWH-081 JWH-098 JWH-116 JWH-122 JWH-149 JWH-164 JWH-182 JWH-193 JWH-198 JWH-200 JWH-210 JWH-398 JWH-424 MAM-1220 MAM-2201 NE-CHMIMO

Naphthoylindazoles

THJ-018 THJ-2201

Pyrrolobenzoxazines

WIN 55,212-2

Naphthylmethylindoles

JWH-175 JWH-176 JWH-184 JWH-185 JWH-192 JWH-194 JWH-195 JWH-196 JWH-197 JWH-199

Phenylacetylindoles

Cannabipiperidiethanone JWH-167 JWH-203 JWH-249 JWH-250 JWH-251 JWH-302 RCS-8

Indole-3-carboxamides

5F-ADBICA 5F-NNE1 5F-PCN 5F-SDB-006 AB-FUBICA AB-PICA ADBICA ADB-FUBICA APICA CUMYL-BICA CUMYL-PICA CUMYL-5F-PICA FDU-NNE1 MDMB-CHMICA MMB-2201 MN-25
MN-25
(UR-12) NNE1 PX-1 Org 28312 Org 28611 SDB-006 STS-135

Indole-3-carboxylates

5F-PB-22 FDU-PB-22 FUB-PB-22 QUCHIC
QUCHIC
(BB-22) QUPIC
QUPIC
(PB-22) NM-2201

Tetramethylcyclo- propanoylindoles

5Br-UR-144 5Cl-UR-144 A-796,260 A-834,735 FUB-144 UR-144 XLR-11 XLR-12

Indazole-3- carboxamides

5Cl-APINACA 5F-ADB 5F-ADB-PINACA 5F-AMB 5F-APINACA 5F-CUMYL-PINACA 5F-EMB-PINACA AB-CHMINACA AB-FUBINACA AB-FUBINACA
AB-FUBINACA
2-fluorobenzyl isomer AB-PINACA ADB-CHMINACA ADB-FUBINACA ADB-PINACA ADAMANTYL-THPINACA ADSB-FUB-187 AMB-CHMINACA AMB-FUBINACA APINACA
APINACA
(AKB48) APP-FUBINACA CUMYL-4CN-BINACA CUMYL-PINACA CUMYL-THPINACA EMB-FUBINACA FUB-APINACA MDMB-FUBINACA MDMB-CHMINACA MN-18 PX-2 PX-3

Tetramethylcyclo- propanoylindazoles

FAB-144

Naphthoylpyrroles

JWH-030 JWH-147 JWH-307 JWH-369 JWH-370

Eicosanoids

AM-883 AM-1346 ACEA ACPA Methanandamide
Methanandamide
(AM-356) O-585 O-689 O-1812 O-1860 O-1861

Pyrazolecarboxamides

5F-AB-FUPPYCA AB-CHFUPYCA AB-CHMFUPPYCA

Others

4-HTMPIPO 5F-PY-PICA 5F-PY-PINACA 5F-3-pyridinoylindole A-836,339 A-955,840 Abnormal cannabidiol AB-001 BzODZ-EPyr AM-1248 AM-1714 AZ-11713908 BAY 38-7271 BAY 59-3074 BIM-018 CB-13 CB-86 CBS-0550 CUMYL-4CN-B7AICA CUMYL-5F-P7AICA CUMYL-PEGACLONE FUBIMINA GSK-554,418A GW-842,166X JTE 7-31 LASSBio-881 LBP-1 Leelamine MDA-7 MDA-19 MEPIRAPIM NESS-040C5 NMP-7 O-889 O-1269 O-1270 O-1399 O-1602 O-2220 PF-03550096 PSB-SB-1202 PTI-1 PTI-2 QMPSB S-444,823 SER-601 Tedalinab URB-447 VSN-16 WIN 56,098

Allosteric CBR ligands

Org 27569 Org 27759 Org 29647 RTI-371 Pregnenolone

Endocannabinoid enhancers (inactivation inhibitors)

4-Nonylphenylboronic acid AM-404 Arachidonoyl serotonin Arvanil BIA 10-2474 Biochanin A CAY-10401 CAY-10429 Genistein Guineesine IDFP JNJ 1661010 JNJ-42165279 JZL184 JZL195 Kaempferol LY-2183240 MK-4409 O-1624 O-2093 Oleoylethanolamide
Oleoylethanolamide
(OEA) Olvanil Palmitoylethanolamide
Palmitoylethanolamide
(PEA) PF-04457845 PF-622 PF-750 PF-3845 PHOP URB-447 URB-597 URB-602 URB-754 VDM-11

Anticannabinoids (antagonists/inverse agonists/antibodies)

AM-251 AM-281 AM-630 AM-1387 AM-4113 AM-6527 AM-6545 BML-190 Brizantin (Бризантин) CAY-10508 CB-25 CB-52 CB-86 Dietressa (Диетресса) Drinabant
Drinabant
(AVE1625) Hemopressin Ibipinabant
Ibipinabant
(SLV319) JTE-907 LH-21 LY-320,135 MDA-77 MJ-15 MK-9470 NESS-0327 NIDA-41020 O-606 O-1184 O-1248 O-1918 O-2050 O-2654 Otenabant
Otenabant
(CP-945,598) PF-514273 PipISB PSB-SB-487 Rimonabant
Rimonabant
(SR141716) Rosonabant
Rosonabant
(E-6776) SR-144,528 Surinabant
Surinabant
(SR147778) Taranabant
Taranabant
(MK-0364) TM-38837 VCHSR

See also: Cannabinoid
Cannabinoid
receptor modulators (cannabinoids by pharmacology) List of: AM cannabinoids JWH cannabinoids Designer drugs § Synthetic cannabimimetics

v t e

Hallucinogens

Psychedelics (5-HT2A agonists)

Benzofurans

2C-B-FLY 2CBFly-NBOMe 5-MeO-BFE 5-MeO-DiBF Bromo-DragonFLY F-2 F-22 TFMFly

Lyserg‐ amides

1P-ETH-LAD 1P-LSD 2-Butyllysergamide 3-Pentyllysergamide AL-LAD ALD-52 BU-LAD Diallyllysergamide Dimethyllysergamide Ergometrine ETH-LAD IP-LAD LAE-32 LPD-824 LSA LSD LSD-Pip LSH LSM-775 LSZ Methylergometrine Methylisopropyllysergamide Methysergide MLD-41 PARGY-LAD PRO-LAD

Phenethyl‐ amines

2C-x

2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V

25x-NBx

25x-NB3OMe

25B-NB3OMe 25C-NB3OMe 25D-NB3OMe 25E-NB3OMe 25H-NB3OMe 25I-NB3OMe 25N-NB3OMe 25P-NB3OMe 25T2-NB3OMe 25T4-NB3OMe 25T7-NB3OMe 25TFM-NB3OMe

25x-NB4OMe

25B-NB4OMe 25C-NB4OMe 25D-NB4OMe 25E-NB4OMe 25H-NB4OMe 25I-NB4OMe 25N-NB4OMe 25P-NB4OMe 25T2-NB4OMe 25T4-NB4OMe 25T7-NB4OMe 25TFM-NB4OMe

25x-NBF

25B-NBF 25C-NBF 25D-NBF 25E-NBF 25H-NBF 25I-NBF 25P-NBF 25T2-NBF 25T7-NBF 25TFM-NBF

25x-NBMD

25B-NBMD 25C-NBMD 25D-NBMD 25E-NBMD 25F-NBMD 25H-NBMD 25I-NBMD 25P-NBMD 25T2-NBMD 25T7-NBMD 25TFM-NBMD

25x-NBOH

25B-NBOH 25C-NBOH 25CN-NBOH 25D-NBOH 25E-NBOH 25F-NBOH 25H-NBOH 25I-NBOH 25P-NBOH 25T2-NBOH 25T7-NBOH 25TFM-NBOH

25x-NBOMe

25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25P-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe

Atypical structures

25I-NB34MD 2CBCB-NBOMe 2CBFly-NBOMe NBOMe-mescaline

3C-x

3C-AL 3C-BZ 3C-DFE 3C-E 3C-P

4C-x

4C-B 4C-D 4C-T-2

DOx

DOT DOB DOC DOEF DOET DOF DOI DOiPR DOM DON DOPR DOTFM MEM

HOT-x

HOT-2 HOT-7 HOT-17

MDxx

DMMDA DMMDA-2 Lophophine MDA MMDA MMDA-2 MMDA-3a MMDMA

Mescaline
Mescaline
(subst.)

2-Bromomescaline 3-TE 4-TE 3-TM 4-TM Allylescaline Asymbescaline Buscaline Cyclopropylmescaline Difluoromescaline Difluoroescaline Escaline Fluoroproscaline Isobuscaline Isoproscaline Jimscaline Mescaline Metaescaline Methallylescaline Proscaline Thioproscaline Trifluoroescaline Trifluoromescaline

TMAs

TMA TMA-2 TMA-3 TMA-4 TMA-5 TMA-6

Others

2C-B-BUTTERFLY 2C-B-DragonFLY 2CB-5-hemifly 2-TOM 5-TOET 5-TOM 2CB-Ind 2CD-5EtO BOB BOD βk-2C-B βk-2C-I DESOXY DMCPA DMBMPP DOB-FLY Fenfluramine Ganesha Macromerine MMA TCB-2 TOMSO

Piperazines

BZP pFPP

Tryptamines

alpha-alkyltryptamines

4,5-DHP-α-MT 5-MeO-α-ET 5-MeO-α-MT α-ET α-MT

x-DALT

(Daltocin) 4-HO-DALT (Daltacetin) 4-AcO-DALT 5-MeO-DALT DALT

x-DET

(Ethacetin) 4-AcO-DET (Ethocin) 4-HO-DET 5-MeO-DET (T-9) DET (Ethocybin) 4-PO-DET

x-DiPT

1-Me-5-MeO-DiPT (Ipracetin) 4-AcO-DiPT (Iprocin) 4-HO-DiPT (Foxy Methoxy) 5-MeO-DiPT DiPT

x-DMT

4,5-DHP-DMT 2,N,N-TMT 4-AcO-DMT 4-HO-5-MeO-DMT 4,N,N-TMT 4-Propionyloxy-DMT 5,6-diBr-DMT 5-AcO-DMT 5-Bromo-DMT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-α,N,N-TMT 5-MeO-DMT 5-N,N-TMT 7,N,N-TMT α,N,N-TMT (Bufotenin) 5-HO-DMT DMT Norbaeocystin (Psilocin) 4-HO-DMT (Psilocybin) 4-PO-DMT

x-DPT

(Depracetin) 4-AcO-DPT (Deprocin) 4-HO-DPT 5-MeO-DPT (The Light) DPT

Ibogaine-related

18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine

x-MET

(Metocin) 4-HO-MET (Metocetin) 4-AcO-MET 5-MeO-MET MET

x-MiPT

(Mipracetin) 4-AcO-MiPT (Miprocin) 4-HO-MiPT 5-Me-MiPT (Moxy) 5-MeO-MiPT MiPT

Others

4-HO-DBT 4-HO-EPT 4-HO-McPT (Lucigenol) 4-HO-MPMI (Meprocin) 4-HO-MPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MPMI Aeruginascin Baeocystin DBT DCPT EiPT EPT MPT PiPT

Others

5-MeO-DiBF AL-38022A ALPHA Dimemebfe Efavirenz Lorcaserin M-ALPHA RH-34 Also empathogens in general (e. g.: 5-APB, 5-MAPB, 6-APB
6-APB
and other substituted benzofurans, MDAI, MDMA).

Dissociatives (NMDAR antagonists)

Arylcyclo‐ hexylamines

Ketamine-related

2-Fluorodeschloroketamine Arketamine
Arketamine
((R)-ketamine) Deschloroketamine Ethketamine
Ethketamine
(N-Ethylnorketamine) Esketamine
Esketamine
((S)-ketamine) Ketamine Methoxetamine Methoxmetamine Methoxyketamine Norketamine Tiletamine

PCP-related

3'-HO-PCP 3'-MeO-PCE 3'-MeO-PCMo 3'-MeO-PCP BDPC Dieticyclidine
Dieticyclidine
(PCDE) Eticyclidine
Eticyclidine
(PCE) Methoxydine
Methoxydine
(4'-MeO-PCP) PCPr Phencyclidine
Phencyclidine
(PCP) Rolicyclidine
Rolicyclidine
(PCPy) Tenocyclidine
Tenocyclidine
(TCP)

Others

BTCP Gacyclidine PRE-084

Diarylethylamines

Diphenidine Ephenidine Fluorolintane Methoxphenidine

Morphinans

Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan

Others

2-EMSB 2-MDP 8A-PDHQ Aptiganel Budipine Delucemine Dexoxadrol Dizocilpine Etoxadrol Herkinorin Ibogaine Midafotel NEFA Neramexane Nitrous oxide Noribogaine Perzinfotel RB-64 Remacemide Salvinorin A Selfotel Xenon

Deliriants (mAChR antagonists)

Atropine Benactyzine Benzatropine Benzydamine Biperiden BRN-1484501 Brompheniramine BZ CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Chloropyramine Chlorphenamine Clemastine CS-27349 Cyclizine Cyproheptadine Dicycloverine Dimenhydrinate Diphenhydramine Ditran Doxylamine EA-3167 EA-3443 EA-3580 EA-3834 Elemicin Flavoxate Hyoscyamine JB-318 JB-336 Meclozine Mepyramine Myristicin Orphenadrine Oxybutynin Pheniramine Phenyltoloxamine Procyclidine Promethazine Scopolamine Tolterodine Trihexyphenidyl Tripelennamine Triprolidine WIN-2299

Others

Cannabinoids (CB1 agonists)

Natural

THC
THC
(Dronabinol) THCV

Synthetic

AM-x

AM-087 AM-251 AM-279 AM-281 AM-356 AM-374 AM-381 AM-404 AM-411 AM-630 AM-661 AM-678 AM-679 AM-694 AM-735 AM-855 AM-881 AM-883 AM-905 AM-906 AM-919 AM-926 AM-938 AM-1116 AM-1172 AM-1220 AM-1221 AM-1235 AM-1241 AM-1248 AM-1710 AM-1714 AM-1902 AM-2201 AM-2212 AM-2213 AM-2232 AM-2233 AM-2389 AM-3102 AM-4030 AM-4054 AM-4056 AM-4113 AM-6545

CP x

CP 47,497 CP 55,244 CP 55,940 (±)-CP 55,940 (+)-CP 55,940 (-)-CP 55,940

HU-x

HU-210 HU-211 HU-239 HU-243 HU-308 HU-320 HU-331 HU-336 HU-345

JWH-x

JWH-007 JWH-015 JWH-018 JWH-019 JWH-030 JWH-047 JWH-048 JWH-051 JWH-057 JWH-073 JWH-081 JWH-098 JWH-116 JWH-120 JWH-122 JWH-133 JWH-139 JWH-147 JWH-148 JWH-149 JWH-149 JWH-161 JWH-164 JWH-166 JWH-167 JWH-171 JWH-175 JWH-176 JWH-181 JWH-182 JWH-184 JWH-185 JWH-192 JWH-193 JWH-193 JWH-194 JWH-195 JWH-196 JWH-197 JWH-198 JWH-199 JWH-200 JWH-203 JWH-205 JWH-210 JWH-210 JWH-213 JWH-220 JWH-229 JWH-234 JWH-249 JWH-250 JWH-251 JWH-253 JWH-258 JWH-300 JWH-302 JWH-307 JWH-336 JWH-350 JWH-359 JWH-387 JWH-398 JWH-424

Misc. designer cannabinoids

4-HTMPIPO 5F-AB-FUPPYCA 5F-AB-PINACA 5F-ADB 5F-ADB-PINACA 5F-ADBICA 5F-AMB 5F-APINACA 5F-CUMYL-PINACA 5F-NNE1 5F-PB-22 5F-SDB-006 A-796,260 A-836,339 AB-001 AB-005 AB-CHFUPYCA AB-CHMINACA AB-FUBINACA AB-PINACA ADAMANTYL-THPINACA ADB-CHMINACA ADB-FUBINACA ADB-PINACA ADBICA ADSB-FUB-187 AMB-FUBINACA APICA APINACA APP-FUBINACA CB-13 CUMYL-PICA CUMYL-PINACA CUMYL-THPINACA DMHP EAM-2201 FAB-144 FDU-PB-22 FUB-144 FUB-APINACA FUB-JWH-018 FUB-PB-22 FUBIMINA JTE 7-31 JTE-907 Levonantradol MDMB-CHMICA MDMB-CHMINACA MDMB-FUBINACA MEPIRAPIM MAM-2201 MDA-19 MN-18 MN-25 NESS-0327 NESS-040C5 Nabilone Nabitan NM-2201 NNE1 Org 28611 Parahexyl PTI-1 PTI-2 PX-1 PX-2 PX-3 QUCHIC QUPIC RCS-4 RCS-8 SDB-005 SDB-006 STS-135 THC-O-acetate THC-O-phosphate THJ-018 THJ-2201 UR-144 WIN 55,212-2 XLR-11

D2 agonists

Apomorphine Aporphine Bromocriptine Cabergoline Lisuride Memantine Nuciferine Pergolide Phenethylamine Piribedil Pramipexole Ropinirole Rotigotine Salvinorin A Also indirect D2 agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).

GABAA enhancers

CI-966 Eszopiclone Ibotenic acid Muscimol
Muscimol
(Amanita muscaria) Zaleplon Zolpidem Zopiclone

Inhalants (Mixed MOA)

Aliphatic hydrocarbons

Butane Gasoline Kerosene Propane

Aromatic hydrocarbons

Toluene

Ethers

Diethyl ether Enflurane

Haloalkanes

Chlorofluorocarbons Chloroform

κOR agonists

2-EMSB Alazocine Bremazocine Butorphan Butorphanol Cyclazocine Cyclorphan Cyprenorphine Diprenorphine Enadoline Herkinorin Heroin HZ-2 Ibogaine Ketazocine Levallorphan Levomethorphan Levorphanol LPK-26 Metazocine Morphine Nalbuphine Nalmefene Nalorphine Noribogaine Oxilorphan Pentazocine Phenazocine Proxorphan Racemethorphan Racemorphan Salvinorin A Spiradoline Tifluadom U-50488 U-69,593 Xorphanol

Others

Glaucine Isoaminile Noscapine Pukateine

v t e

Cannabinoid
Cannabinoid
receptor modulators

Receptor (ligands)

CB1

Agonists (abridged; see here for more): 2-AG 2-AGE (noladin ether) 11-Hydroxy-THC α-Amyrin β-Amyrin AB-CHMINACA AM-1172 AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 Anandamide Arvanil AZ-11713908 Cannabinol CB-13 CP 47,497 CP 55,940 Dimethylheptylpyran DEA ECG EGCG Epicatechin Gallocatechol
Gallocatechol
(gallocatechin) Honokiol HU-210 JWH-007 JWH-015 JWH-018 JWH-073 Kavain L-759,633 Levonantradol Menabitan Nabilone Nabitan NADA O-1812 Oleamide Pravadoline Serinolamide A THC
THC
(dronabinol) UR-144 WIN 55,212-2 Yangonin

Antagonists: AM-251 AM-6545 Cannabidiol Cannabigerol Drinabant Falcarinol
Falcarinol
(carotatoxin) Hemopressin Ibipinabant LY-320,135 MK-9470 NESS-0327 O-2050 Otenabant PF-514273 PipISB Rimonabant Rosonabant Surinabant Taranabant THCV TM-38837 VCHSR Virodhamine

Antibodies: Brizantin (Бризантин) Dietressa (Диетресса)

Unknown/unsorted: MAFP

CB2

Agonists: 2-AG 2-AGE (noladin ether) 3,3'-Diindolylmethane 4-O-Methylhonokiol α-Amyrin β-Amyrin A-796,260 A-834,735 A-836,339 AM-1172 AM-1221 AM-1235 AM-1241 AM-2232 Anandamide AZ-11713908 Cannabinol Caryophyllene CB-13 CBS-0550 CP-55,940 GW-405,833
GW-405,833
(L-768,242) GW-842,166X HU-308 JTE 7-31 JWH-007 JWH-015 JWH-018 JWH-73 JWH-133 L-759,633 L-759,656 Magnolol MDA-19 Nabitan NADA PF-03550096 S-444,823 SER-601 Serinolamide A UR-144 Tedalinab THC
THC
(dronabinol) THCV Tetrahydromagnolol Virodhamine

Antagonists: 4-O-Methylhonokiol AM-630 BML-190 Cannabidiol Honokiol JTE-907 SR-144,528 WIN 54,461 WIN 56,098

NAGly (GPR18)

Agonists: Abnormal cannabidiol ACPA AM251 Anandamide Cannabidiol NADGly THC
THC
(dronabinol) O-1602

Antagonists: CID-85469571 O-1918

GPR55

Agonists: 2-AGE (noladin ether) 2-ALPI Abnormal cannabidiol AM-251 CID1011163 CID1252842 CID1792579 CP 55,940 GSK-494581A Lysophosphatidylinositol ML-184 ML-185 ML-186 O-1602 Oleoylethanolamide Palmitoylethanolamide THC
THC
(dronabinol)

Antagonists: Cannabidiol CID-16020046 ML-191 ML-192 ML-193 O-1918 PSB-SB-487 PSB-SB-1202 PSB-SB-1203 Tetrahydromagnolol

GPR119

Agonists: 2-Oleoylglycerol Anandamide APD668 AR-231,453 AS-1269574 MBX-2982 N-Oleoyldopamine Oleoylethanolamide Olvanil PSN-375,963 PSN-632,408

Transporter (modulators)

eCBTs

Inhibitors: 5'-DMH-CBD AM-404 AM-1172 Arachidonoyl serotonin Arvanil Cannabidiol Guineensine LY-2183240 O-2093 OMDM-2 Paracetamol
Paracetamol
(acetaminophen) SB-FI-26 UCM-707 URB-597 VDM-11 WOBE490 WOBE491 WOBE492

Enzyme (modulators)

FAAH

Inhibitors: 4-Nonylphenylboronic acid AACOCF3 AM-404 Arachidonoyl serotonin BIA 10-2474 Biochanin A Genistein IDFP JNJ-1661010 JNJ-42165279 JZL-195 Kaempferol LY-2183240 MAFP Palmitoylisopropylamide Paracetamol
Paracetamol
(acetaminophen) PF-3845 PF-04457845 PF-750 SA-47 SA-57 TAK 21d TC-F 2 UCM710 URB-597

Activators: PDP-EA

MAGL

Inhibitors: ABX-1431 IDFP JJKK 048 JW 642 JZL-184 JZL-195 JZP-361 KML 29 MAFP MJN110 NAM Pristimerin URB-602

ABHD6

Inhibitors: JZP-169 JZP-430 KT182 KT185 KT195 KT203 LEI-106 ML294 ML295 ML296 UCM710 WWL-70

ABHD12

Inhibitors: Betulinic acid Maslinic acid MAFP Oleanolic acid Orlistat
Orlistat
(tetrahydrolipstatin) Ursolic acid

Others

Precursors: Phosphatidylethanolamine NAPE Diacylglycerol

Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor) ARN-272 (FAAH-like anandamide transporter inhibitor)

See also Receptor/signaling modulators Cannabinoids
Cannabinoids
(cannabin