JWH-081

JWH-081
Legal status

Legal status	CA: Schedule II DE: Anlage II (Prohibited) US: Schedule I I-N (Poland)^[1]
Identifiers
IUPAC name 4-methoxynaphthalen- 1-yl- (1-pentylindol- 3-yl)methanone
CAS Number	210179-46-7^Y
PubChem (CID)	10547208
ChemSpider	8722599
ECHA InfoCard	100.230.181
Chemical and physical data
Formula	C₂₅H₂₅NO₂
Molar mass	371.47 g/mol
3D model (Jmol)	Interactive image
SMILES CCCCCn3c1ccccc1c(c3)C(=O)c4c2ccccc2c(OC)cc4
InChI InChI=1S/C25H25NO2/c1-3-4-9-16-26-17-22(19-11-7-8-13-23(19)26)25(27)21-14-15-24(28-2)20-12-6-5-10-18(20)21/h5-8,10-15,17H,3-4,9,16H2,1-2H3 Key:UBMPKJKGUQDHRM-UHFFFAOYSA-N
(verify)

JWH-081 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB₁ and CB₂ receptors.^[2] With a K_i of 1.2nM it is fairly selective for the CB₁ subtype, its affinity at this subtype approximately 10x the affinity at CB₂.^[3] It was discovered by and named after Dr. John W. Huffman.

JWH-081 may be neurotoxic to animals when administered in high doses.^[4]

Legal Status

As of October 2015 JWH-081 is a controlled substance in China.^[5]

References

↑ "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii (Dz.U. 2011 nr 105 poz. 614)". Internetowy System Aktów Prawnych. Retrieved 12 June 2011.
↑ Aung MM, et al. Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB₁ and CB₂ receptor binding. Drug and Alcohol Dependence 2000; 60:133-140.
↑ Huffman JW, et al. Structure–activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB₁ and CB₂ receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB₂ receptor agonists. Bioorganic and Medicinal Chemistry. 2005; 13:89-112.
↑ Hye Jin Cha; Yeon-Hee Seong; Min-Ji Song; Ho-Sang Jeong; Jisoon Shin; Jaesuk Yun; Kyoungmoon Han; Young-Hoon Kim; Hoil Kang; Hyoung Soo Kim (November 2015). "Neurotoxicity of Synthetic Cannabinoids JWH-081 and JWH-210". Biomolecules & Therapeutics. 23 (6): 597–603. doi:10.4062/biomolther.2015.057. PMC 4624077. PMID 26535086.
↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.

Cannabinoids

Phytocannabinoids

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

Endocannabinoids

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 (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 (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 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 HUF-102 HUF-103 Nonabine O-1376 O-1422 O-1601 O-1656 O-1657 O-1660 O-1663 O-1871 SPA-229 Tinabinol 2-Isopropyl-5-methyl-1- (2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene

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 (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 (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 (BB-22) 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 2-fluorobenzyl isomer AB-PINACA ADB-CHMINACA ADB-FUBINACA ADB-PINACA ADAMANTYL-THPINACA ADSB-FUB-187 AMB-CHMINACA AMB-FUBINACA APINACA (AKB48) APP-FUBINACA 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 (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 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)

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 (AVE1625)
Hemopressin
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 (CP-945,598)
PF-514273
PipISB
PSB-SB-487
Rimonabant (SR141716)
Rosonabant (E-6776)
SR-144,528
Surinabant (SR147778)
Taranabant (MK-0364)
TM-38837
VCHSR

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

Hallucinogens

Psychedelics
(5-HT_2A
agonists)

Lyserg‐
amides

Phenethyl‐
amines

2C-*	2C-B 2C-B-AN 2C-C 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-I 2C-iP 2C-N 2C-O 2C-O-4 2C-P 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-7 2C-T-8 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-19 2C-T-21 2C-T-21.5 2C-T-22 2C-T-27 2C-T-28 2C-TFM 2C-YN TMA-2

HOT-*	HOT-2 HOT-7 HOT-17

25-NB (excludes FLY)	-NBF: 25B-NBF 25C-NBF 25I-NBF -NBOH: 25B-NBOH 25C-NBOH 25CN-NBOH 25I-NBOH -NBMD: 25B-NBMD 25C-NBMD 25I-NB34MD 25I-NBMD -NBOMe: 25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25I-NBOMe 25N-NBOMe 25P-NBOMe 25TFM-NBOMe

Subst. mescaline	2-Bromomescaline Allylescaline Asymbescaline Buscaline Cyclopropylmescaline Difluoromescaline Difluoroescaline Escaline Fluoroproscaline Isobuscaline Isoproscaline Mescaline Metaescaline Methallylescaline Proscaline Trifluoroescaline Trifluoromescaline

DO*	(DOT) Aleph DOB DOC DOEF DOET DOF DOI DOiPR DOM DON DOPR DOTFM MEM

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

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

FLY	2CBFly-NBOMe 2C-B-DragonFLY 2C-B-BUTTERFLY 2C-B-FLY Bromo-DragonFLY DOB-FLY TFMFly

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

Others	βk-2C-B βk-2C-I 2CB-Ind 2CD-5EtO 2CBCB-NBOMe 2-TOM 3-TE 3-TM 4-TE 4-TM 5-TOET 5-TOM BOB BOD DESOXY DMBMPP DMCPA Fenfluramine Ganesha Jimscaline Macromerine MMA NBOMe-mescaline TCB-2 Thioproscaline TOMSO TMA

Piperazines

Tryptamines

Sub. Trypt.	4,5-DHP-α-MT 5-MeO-α-ET 5-MeO-α-MT α-ET α-MT

*-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

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

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

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

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

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

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

Subst. Ibogamine	Ibogaine Noribogaine Voacangine

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 and other substituted benzofurans, MDAI, MDMA).

Dissociatives
(NMDAR
antagonists)

Arylcyclo‐ hexylamines	2-Fluorodeschloroketamine 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP Arketamine Deschloroketamine Dieticyclidine Esketamine Ethketamine Eticyclidine Gacyclidine Ketamine Methoxetamine Methoxmetamine Methoxyketamine Norketamine PCPr PCP Rolicyclidine Tenocyclidine Tiletamine

Morphinans	Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan

Diarylethylamines	Diphenidine Ephenidine Fluorolintane Methoxphenidine

Others	2-MDP 8A-PDHQ Aptiganel Budipine Delucemine Dexoxadrol Dizocilpine Etoxadrol Ibogaine Midafotel NEFA Neramexane Nitrous oxide Noribogaine Perzinfotel Remacemide Selfotel Xenon

Deliriants
(mAChR
antagonists)

Others

Cannabinoids
(CB₁ agonists)

Natural	Cannabinol THC (Dronabinol) THCV

Synthetic	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 AM-630 AM-679 AM-694 AM-1220 AM-1221 AM-1235 AM-1241 AM-1248 AM-2201 AM-2232 AM-2233 AMB-FUBINACA APICA APINACA APP-FUBINACA CB-13 CP 47,497 CP 55,244 CP 55,940 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 HU-210 HU-308 JWH-007 JWH-015 JWH-018 JWH-019 JWH-030 JWH-073 JWH-081 JWH-098 JWH-116 JWH-122 JWH-149 JWH-167 JWH-182 JWH-193 JWH-198 JWH-200 JWH-203 JWH-210 JWH-250 JWH-251 JWH-398 JWH-424 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).

GABA_A
enhancers

Inhalants
(Mixed MOA)

κOR agonists

Others

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JWH-081

Legal Status

See also

References