Nonabine

Nonabine

Systematic (IUPAC) name
7-(1,2-dimethylheptyl)-2,2-dimethyl-4-(4-pyridinyl)-2H-1-benzopyran-5-ol
Identifiers
CAS Number	16985-03-8
ATC code	none
PubChem	CID 71885
ChemSpider	64899
UNII	77DUK856J7
Chemical data
Formula	C25H33NO2
Molar mass	379.534 g/mol
SMILES CCCCCC(C)C(C)c1cc(c2c(c1)OC(C=C2c3ccncc3)(C)C)O
InChI InChI=1S/C25H33NO2/c1-6-7-8-9-17(2)18(3)20-14-22(27)24-21(19-10-12-26-13-11-19)16-25(4,5)28-23(24)15-20/h10-18,27H,6-9H2,1-5H3 Key:YHUDSHIRWOVVCV-UHFFFAOYSA-N
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Nonabine (BRL-4664) is a drug which is a cannabinoid derivative, which was developed for the prevention of nausea and vomiting associated with cancer chemotherapy.^[1] It has strong antiemetic effects equivalent to those of chlorpromazine, and also produces some mild sedative effects, along with dry mouth and EEG changes typical of cannabinoid agonists, but with minimal changes in mood or perception, suggesting the abuse potential is likely to be low.^[2][3]

References

1. Staquet M, Bron D, Rozencweig M, Kenis Y. Clinical studies with a THC analog (BRL-4664) in the prevention of cisplatin-induced vomiting. Journal of Clinical Pharmacology. 1981 Aug-Sep;21(8-9 Suppl):60S-63S. PMID 7197692
2. Archer CB, Amlot PL, Trounce JR. Antiemetic effect of nonabine in cancer chemotherapy: a double blind study comparing nonabine and chlorpromazine. British Medical Journal (Clinical Research Edition). 1983 Jan 29;286(6362):350-1. PMID 6402096
3. McClelland GR, Sutton JA. Pilot investigation of the quantitative EEG and clinical effects of ketazolam and the novel antiemetic nonabine in normal subjects. Psychopharmacology (Berlin). 1985;85(3):306-8. PMID 2860687