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Chemical compound
Menabitan
ATC code
Legal status
[5,5-dimethyl-8-(3-methyloctan-2-yl)-2-prop-2-ynyl-3,4-dihydro-1H -chromeno[4,3-c]pyridin-10-yl] 2-methyl-4-(2-methylpiperidin-1-yl)butanoate
CAS Number
PubChem
CID
ChemSpider
UNII
CompTox Dashboard (
EPA )
Formula C 37 H 56 N 2 O 3
Molar mass 576.866 g·mol−1 3D model (
JSmol )
CCCCCC(C)C(C)C1=CC2=C(C3=C(CCN(C3)CC#C)C(O2)(C)C)C(=C1)OC(=O)C(C)CCN4CCCCC4C
InChI=1S/C37H56N2O3/c1-9-11-12-15-26(3)29(6)30-23-33(41-36(40)27(4)17-22-39-20-14-13-16-28(39)5)35-31-25-38(19-10-2)21-18-32(31)37(7,8)42-34(35)24-30/h2,23-24,26-29H,9,11-22,25H2,1,3-8H3
Key:ZWLPJYVIMWAEDC-UHFFFAOYSA-N
Menabitan (
INN ; SP-204 ), or menabitan hydrochloride (
USAN ), is a
synthetic
drug which acts as a
potent
cannabinoid receptor
agonist .
[1]
[2] It is closely related to
natural
cannabinoids of the
tetrahydrocannabinol (THC) group, differing mainly by its longer and branched
side chain , and the replacement of the 9-position carbon with a nitrogen. It's a structural analog of
Nabitan and
Dimethylheptylpyran .
[1] It was studied as an
analgesic in the 1970s and was found to possess
antinociceptive effects in both humans and animals but was never marketed.
[1]
[3]
[4]
Due to its structural similarity to the Schedule I/III drug THC it can be treated as a Schedule I drug within the United States legal system under the
Federal Analogue Act .
See also
References
Phytocannabinoids (
comparison )
Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabiphorols Cannabinols Cannabitriols Cannabivarins Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols Delta-10-Tetrahydrocannabinols Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols
Eicosanoids
Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles
Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Tetramethylcyclo- propylindoles Others
Allosteric
CBR Tooltip Cannabinoid receptor
ligands
Endocannabinoid enhancers (inactivation inhibitors)
Anticannabinoids (antagonists/inverse agonists/antibodies)
Receptor (
ligands )
CB1 Tooltip Cannabinoid receptor type 1
Agonists(abridged,
full list ) Inverse agonists Antagonists
CB2 Tooltip Cannabinoid receptor type 2
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 (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
Lenabasum (anabasum)
Magnolol
MDA-19
Nabitan
NADA
Olorinab (APD-371)
PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
THC (dronabinol)
THCV
Tetrahydromagnolol
Virodhamine
Antagonists
NAGly (
GPR18 )
GPR55
GPR119
Transporter (
modulators )
eCBTs Tooltip Endocannabinoid transporter
Enzyme (
modulators )
Others
Others:
2-PG (directly potentiates activity of 2-AG at CB1 receptor)
ARN-272 (FAAH-like anandamide transporter inhibitor)