Nabitan

Nabitan
Clinical data
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;
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 ;

Nabitan (Nabutam, Benzopyranoperidine, SP-106, Abbott 40656) is a synthetic cannabinoid analog of dronabinol (Marinol).^[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.

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[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]

Clinical data

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^Y
PubChem CID	39503
ChemSpider	36117^Y
UNII	JO7BOR6B3O
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^Y Key:MCVPMHDADNVRKF-UHFFFAOYSA-N^Y