Nabitan

Nabitan
Clinical data
Other names	Nabutam, benzopyranoperidine, SP-106, Abbott 40656
Drug class	Cannabinoid
ATC code	none;
Identifiers
	IUPAC name 5,5-Dimethyl-8-(3-methyloctan-2-yl)-2-(prop-2-yn-1-yl)-1,3,4,5-tetrahydro-2H-[1]benzopyrano[4,3-c]pyridin-10-yl 4-(piperidin-1-yl)butanoate;
CAS Number	66556-74-9 ;
PubChem CID	39503;
ChemSpider	36117 ;
UNII	JO7BOR6B3O;
CompTox Dashboard (EPA)	DTXSID40867230 ;
Chemical and physical data
Formula	C35H52N2O3
Molar mass	548.812 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(Oc2cc(cc1OC(C\3=C(/c12)CN(CC/3)CC#C)(C)C)C(C)C(C)CCCCC)CCCN4CCCCC4;
	InChI InChI=1S/C35H52N2O3/c1-7-9-11-15-26(3)27(4)28-23-31(39-33(38)16-14-21-36-19-12-10-13-20-36)34-29-25-37(18-8-2)22-17-30(29)35(5,6)40-32(34)24-28/h2,23-24,26-27H,7,9-22,25H2,1,3-6H3 ; Key:MCVPMHDADNVRKF-UHFFFAOYSA-N ;
	(verify)

Nabitan (nabutam, benzopyranoperidine, SP-106, Abbott 40656) is a synthetic cannabinoid analog of dronabinol (Δ⁹-tetrahydrocannabinol) and dimethylheptylpyran.^[1] It exhibits antiemetic and analgesic effects, most likely by binding to and activating the CB₁ and CB₂ cannabinoid receptors, and reduced intraocular pressure in animal tests, making it potentially useful in the treatment of glaucoma.^[2]

Nabitan has the advantage of being water-soluble, unlike most cannabinoid derivatives, and was researched for potential use as an analgesic or sedative,^[3] although it was never developed for clinical use and is not currently used in medicine, as dronabinol or nabilone were felt to be more useful. However, it is sometimes used in research into the potential therapeutic applications of cannabinoids.

References

^ Razdan RK. The Total Synthesis of Cannabinoids. Wiley-Interscience 1980
^ Razdan RK, Howes JF (1983). "Drugs related to tetrahydrocannabinol". Medicinal Research Reviews. 3 (2): 119–46. doi:10.1002/med.2610030203. PMID 6134882. S2CID 31313909.
^ Archer RA (1974). "The cannabinoids: therapeutic potentials". Annual Reports in Medicinal Chemistry. 9: 253–9. doi:10.1016/s0065-7743(08)61448-7. PMID 12307093.

[1] Razdan RK. The Total Synthesis of Cannabinoids. Wiley-Interscience 1980

[2] Razdan RK, Howes JF (1983). "Drugs related to tetrahydrocannabinol". Medicinal Research Reviews. 3 (2): 119–46. doi:10.1002/med.2610030203. PMID 6134882. S2CID 31313909.

[3] Archer RA (1974). "The cannabinoids: therapeutic potentials". Annual Reports in Medicinal Chemistry. 9: 253–9. doi:10.1016/s0065-7743(08)61448-7. PMID 12307093.

[1]

[2]

[3]

Hallucinogens
Psychedelics (5-HT_2A agonists)	Tryptamines (e.g., DMT, psilocin, psilocybin, bufotenin, 5-MeO-DMT, AMT) Phenethylamines (e.g., mescaline, 2C-B, DOM, MDA, TMA, 2C-B-FLY, 25I-NBOMe) Lysergamides (e.g., LSD, ergine, isoergine) Others (e.g., efavirenz, IHCH-7113, MK-212, quipazine, RH-34) For a full list of serotonergic psychedelics, see the navbox here and the list here instead.
Dissociatives (NMDA antagonists)	Arylcyclohexylamines (e.g., ketamine (K), phencyclidine (PCP), methoxetamine (MXE), tiletamine) Adamantanes (e.g., memantine, amantadine) Diarylethylamines (e.g., diphenidine, ephenidine, methoxphenidine) Morphinans (e.g., dextromethorphan (DXM), dextrorphan (DXO)) Inhalants (e.g., nitrous oxide (N₂O), xenon (Xe)) Others (e.g., alkyl nitrites/poppers, aptiganel, dexoxadrol, dizocilpine (MK-801), etoxadrol, selfotel) For a full list of dissociatives, see the navbox here instead.
Deliriants (mACh antagonists)	Tropanes: Atropine Hyoscyamine Scopolamine (hyoscine) Antihistamines: Brompheniramine Chloropyramine Chlorphenamine (chlorpheniramine) Clemastine Cyclizine Cyproheptadine Dimenhydrinate Diphenhydramine Doxylamine Meclizine Mepyramine Pheniramine Phenyltoloxamine Promethazine Tripelennamine Triprolidine Others: Benactyzine Benapryzine (benaprizine) Benzatropine (benztropine) Biperiden BZ (QNB) CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,668 CS-27349 Cycrimine Dicycloverine Ditran (JB-329) EA-3167 EA-3443 EA-3580 EA-3834 Flavoxate JB-318 JB-336 Orphenadrine Oxybutynin Procyclidine Tolterodine Trihexyphenidyl Tropicamide Tropine benzilate WIN-2299
KOR agonists	Salvinoids (terpenoids): 2-EMSB 2-MMSB RB-64 (22-thiocyanatosalvinorin A) Salvinorin A Benzomorphans: Alazocine Bremazocine Cyclazocine Ketazocine Metazocine MR-2034 Pentazocine Phenazocine Morphinans: Butorphanol Cyclorphan Cyprenorphine Diprenorphine Heroin Levallorphan Levomethorphan Levorphanol Morphine Nalbuphine Nalmefene Nalorphine Oxilorphan Proxorphan Racemethorphan Racemorphan Xorphanol Arylacetamides: Enadoline LPK-26 Niravoline Spiradoline U-50488 U-69593 Others: HZ-2 Tifluadom
GABA_A agonists	Isoxazoles: Gaboxadol (THIP) Ibotenic acid (Amanita muscaria) Muscimol (Amanita muscaria) Indirect GABA_A receptor agonists: GABA_A receptor positive allosteric modulators (nonbenzodiazepines/Z-drugs) (e.g., eszopiclone, zaleplon, zolpidem, zopiclone) GABA reuptake inhibitors (e.g., CI-966)
Oneirogens (unknown mech.)	Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis caapi) Iboga alkaloids/azepinoindoles (e.g., ibogaine, noribogaine) (found in Tabernanthe iboga)
Cannabinoids (CB₁ agonists)	Phytocannabinoids (e.g., Δ⁹-THC (dronabinol), CBN, Δ⁸-THC) Synthetic cannabinoids (e.g., nabilone, JWH-018, JWH-073, HU-210) For a full list of cannabinoids, see the navbox here and the list here instead.
Others	Aminochromes (e.g., adrenochrome, adrenolutin) Carbogen Glaucine Hallucinogenic bolete mushrooms (e.g., Lanmaoa asiatica) Jenkem Kykeon (Eleusinian Mysteries) Nutmeg (e.g., myristicin, elemicin) Soma (haoma)
See also: Psychedelics Dissociatives Entactogens Stimulants Depressants List of hallucinogens

See also

References