Menabitan ATC code Legal status
US : Analogue to a Schedule I/II drug (Schedule I)
[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.[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 [ ]
^ a b c Green K, Kim K (February 1977). "Acute dose response of intraocular pressure to topical and oral cannabinoids". Proceedings of the Society for Experimental Biology and Medicine . 154 (2): 228–31. doi :10.3181/00379727-154-39643 . PMID 402656 . S2CID 32785623 .
^ Triggle DJ (1996). Dictionary of Pharmacological Agents . Boca Raton: Chapman & Hall/CRC. p. 1271. ISBN 978-0-412-46630-4 .
^ Reggio PH (1987). "Molecular determinants for cannabinoid activity: refinement of a molecular reactivity template". NIDA Research Monograph . 79 : 82–95. PMID 2830539 .
^ Gabriel G. Nahas (5 April 1999). Marihuana and Medicine . Humana Press. p. 46. ISBN 978-0-89603-593-5 . Retrieved 9 May 2012 .
Analgesics (N02A , N02B )
Opioids
Opiates /opium
Codeine #
Morphine # (+naltrexone )
Opium
Laudanum
Paregoric
Semisynthetic
Acetyldihydrocodeine
Benzylmorphine
Buprenorphine (+naloxone )
Butorphanol
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NFEPP
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Tapentadol
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Paracetamol -type
Acetanilide ‡
Bucetin ‡
‡
Paracetamol (acetaminophen) #
+aspirin/caffeine
+codeine
+hydrocodone
+metoclopramide
+oxycodone
+propyphenazone/caffeine
‡
Phenacetin ‡
Propacetamol ‡
NSAIDs
Propionates
Benoxaprofen ‡
Fenoprofen
Flurbiprofen
Ibuprofen # (Dexibuprofen )
Ketoprofen (Dexketoprofen )
Loxoprofen
Naproxen
Oxaprozin
Suprofen
Tiaprofenic acid
Zaltoprofen
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Acemetacin
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Etodolac
Indometacin (Indometacin farnesil )
Ketorolac
Sulindac
Tolmetin
Zomepirac ‡
COX-2 inhibitors Fenamates
Flufenamic acid
Meclofenamic acid
Mefenamic acid
Tolfenamic acid
Salicylates
Aspirin (acetylsalicylic acid) # (+paracetamol/caffeine )
Aloxiprin
Benorylate
Carbasalate calcium
Choline salicylate
Diflunisal
Dipyrocetyl
Ethenzamide
Guacetisal
Imidazole salicylate
Magnesium salicylate
Morpholine salicylate
Potassium salicylate
Salicin
Salicylamide
Salsalate
Sodium salicylate
Wintergreen (methyl salicylate )
Pyrazolones
Aminophenazone ‡
Ampyrone
Metamizole (dipyrone)
Nifenazone
Phenazone
Propyphenazone (+paracetamol/caffeine )
Others
Benzydamine
Floctafenine
Glafenine
Nabumetone
Nimesulide
Proquazone
Cannabinoids
Cannabidiol
Cannabis
Nabilone
Nabiximols
Tetrahydrocannabinol (dronabinol)
Ion channel modulators
Calcium blockers
Alcohol (ethanol)
Gabapentin
Gabapentin enacarbil
Leconotide
Mirogabalin
Pregabalin
Ziconotide
Sodium blockers
Carbamazepine
Lacosamide
Local anesthetics (e.g., cocaine , lidocaine )
Mexiletine
Nefopam
Tricyclic antidepressants (e.g., amitriptyline # )
Nav 1.7/1.8-selective: DSP-2230 §
Funapide §
PF-05089771 §
Potassium openers
Myorelaxants
Carisoprodol
Chlorzoxazone
Cyclobenzaprine
Mephenoxalone
Methocarbamol
Orphenadrine
Others
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
Cannabinoids
Phytocannabinoids
Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabinols and cannabinodiols Cannabitriols Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols
Delta-9-THC (THC)
THCH
THCP
THCV
Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Arachidonoyl ethanolamide (AEA; anandamide)
2-Arachidonoylglycerol (2-AG)
2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
2-Oleoylglycerol (2-OG)
N-Arachidonoyl dopamine (NADA)
N-Arachidonylglycine (NAGly)
N-Arachidonoyl serotonin (AA-5-HT)
Docosatetraenoylethanolamide (DEA)
Lysophosphatidylinositol (LPI)
Oleamide
Oleoylethanolamide (OEA)
Palmitoylethanolamide (PEA)
RVD-Hpα
Stearoylethanolamide (SEA)
O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles
AM-630
AM-679
AM-694
AM-1241
AM-2233
GW-405,833 (L-768,242)
Pravadoline
RCS-4
WIN 54,461
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
A-796,260
A-834,735
FUB-144
UR-144
XLR-11
XLR-12
Tetramethylcyclo- propylindoles Others
Allosteric CBR ligands Endocannabinoid enhancers (inactivation inhibitors) Anticannabinoids (antagonists/inverse agonists/antibodies)
AM-251
AM-630
AM-6545
BML-190
Drinabant (AVE1625)
Hemopressin
Ibipinabant (SLV319)
JTE-907
LY-320,135
MK-9470
NESS-0327
O-1918
O-2050
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: Cannabinoid receptor modulators (cannabinoids by pharmacology)
List of: AM cannabinoids
JWH cannabinoids
Designer drugs § Synthetic cannabimimetics
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-1220
AM-1221
AM-1235
AM-2201
AM-2232
Anandamide
AZ-11713908
Cannabinol
CB-13
CP 47,497
CP 55,940
Dimethylheptylpyran
DEA
ECG
EGCG
Epicatechin
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 (dronabinol)
UR-144
WIN 55,212-2
Yangonin
Antagonists: AM-251
AM-6545
Cannabidiol
Cannabigerol
Drinabant
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
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-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-133
L-759,633
L-759,656
Magnolol
MDA-19
Nabitan
NADA
Olorinab (APD-371)
PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
THC (dronabinol)
THCV
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 (dronabinol)
O-1602
GPR55
Agonists: 2-AGE (noladin ether)
Abnormal cannabidiol
AM-251
CP 55,940
Lysophosphatidylinositol
O-1602
Oleoylethanolamide
Palmitoylethanolamide
THC (dronabinol)
GPR119 Unsorted
Transporter (modulators )
eCBTs
Inhibitors:
AM-404
Arachidonoyl serotonin
Cannabidiol
Guineensine
LY-2183240
Paracetamol (acetaminophen)
URB-597
VDM-11
Enzyme (modulators )
FAAH MAGL
Inhibitors:
IDFP
JZL-184
JZL-195
MAFP
URB-602
ABHD6 ABHD12
Inhibitors: Betulinic acid
Maslinic acid
MAFP
Oleanolic acid
Orlistat (tetrahydrolipstatin)
Ursolic acid
Others
Precursors: Phosphatidylethanolamine
NAPE
Diacylglycerol
Others: (directly potentiates activity of 2-AG at CB1 receptor)
(FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)