Alazocine

Alazocine
Clinical data

Routes of administration	?
ATC code	none
Legal status
Legal status	Uncontrolled
Identifiers
IUPAC name (2R,6R,11R)-6,11-Dimethyl-3-prop-2-en-1-yl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol
CAS Number	14198-28-8^N
PubChem (CID)	3036246
ChemSpider	2300306^Y
ChEMBL	CHEMBL330376^Y
ECHA InfoCard	100.162.264
Chemical and physical data
Formula	C₁₇H₂₃NO
Molar mass	257.37 g/mol
3D model (Jmol)	Interactive image
SMILES C[C@H]1[C@H]2CC3=C([C@@]1(CCN2CC=C)C)C=C(C=C3)O
InChI InChI=1S/C17H23NO/c1-4-8-18-9-7-17(3)12(2)16(18)10-13-5-6-14(19)11-15(13)17/h4-6,11-12,16,19H,1,7-10H2,2-3H3/t12-,16+,17+/m0/s1^Y Key:LGQCVMYAEFTEFN-JCURWCKSSA-N^Y
^NY (what is this?)

Alazocine ((-)-SKF-10,047), or (-)-N-allylnormetazocine ((-)-ANMC), was the first drug discovered to act as a σ₁ receptor agonist (K_i = 24 nM). It has no significant affinity for the σ₂ receptor. Alazocine also acts as a κ-opioid receptor partial agonist (K_i = 0.4 nM; EC₅₀ = 24 nM; E_max = 66%), and to a much lesser extent, as an NMDA receptor antagonist (K_i = 587 nM).