Dimemorfan

Dimemorfan
Systematic (IUPAC) name
	(4bS,8aS,9S)-3,11-Dimethyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	36309-01-0
ATC code	R05DA11 (WHO)
PubChem	CID: 3037918
ChemSpider	16735785
UNII	623OAC38YU
KEGG	D07848
ChEMBL	CHEMBL2106325
Chemical data
Formula	C18H25N
Molecular mass	255.398 g/mol
	SMILES CC1=CC2=C(C[C@@H]3N(CC[C@@]42CCCC[C@H]34)C)C=C1 ;
	InChI InChI=1S/C18H25N/c1-13-6-7-14-12-17-15-5-3-4-8-18(15,16(14)11-13)9-10-19(17)2/h6-7,11,15,17H,3-5,8-10,12H2,1-2H3/t15-,17+,18+/m1/s1 ; Key:KBEZZLAAKIIPFK-NJAFHUGGSA-N ;
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Dimemorfan (INN) (or dimemorphan) (brand names Astomin, Dastosirr, Tusben), or dimemorfan phosphate (JAN), also known as 3,17-dimethylmorphinan, is an antitussive (cough suppressant) of the morphinan family that is widely used in Japan and is also marketed in Spain and Italy.^[1]^[2]^[3]^[4] It was developed by Yamanouchi Pharmaceutical (now Astellas Pharma) and introduced in Japan in 1975.^[3] Dimemorfan is an analogue of dextromethorphan (DXM) and its active metabolite dextrorphan (DXO), and similarly to them, acts as a potent agonist of the σ₁ receptor (K_i = 151 nM).^[5]^[6] However, unlike DXM and DXO, it does not act significantly as an NMDA receptor antagonist, and for this reason, lacks dissociative effects, thereby having reduced side effects and abuse potential in comparison.^[7]^[8] Similarly to DXM and DXO, dimemorfan has only relatively low affinity for the σ₁ receptor (K_i = 4421 nM).^[6]

References

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