Alazocine

Alazocine

Systematic (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
Clinical data
Routes of administration	?
Legal status
Legal status	Uncontrolled
Identifiers
CAS Number	14198-28-8
ATC code	none
PubChem	CID 3036246
ChemSpider	2300306
ChEMBL	CHEMBL330376
Chemical data
Formula	C17H23NO
Molar mass	257.37 g/mol
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 Key:LGQCVMYAEFTEFN-JCURWCKSSA-N
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Alazocine ((-)-SKF-10,047), or (-)-N-allylnormetazocine ((-)-ANMC), was the first drug discovered to act as a σ₁ receptor agonist (K_i = 24 nM).^[1][2][3] It has no significant affinity for the σ₂ receptor.^[3] Alazocine also acts as a κ-opioid receptor partial agonist (K_i = 0.4 nM; EC₅₀ = 24 nM; E_max = 66%),^[4] and to a much lesser extent, as an NMDA receptor antagonist (K_i = 587 nM).^[3][5]

See also

• Benzomorphan

References

1. Iwamoto ET (February 1981). "Pharmacologic effects of N-allylnormetazocine (SKF-10047)". NIDA Research Monograph 34: 82–8. PMID 6783955.
2. Shearman GT, Herz A (August 1982). "Non-opioid psychotomimetic-like discriminative stimulus properties of N-allylnormetazocine (SKF 10,047) in the rat". European Journal of Pharmacology 82 (3–4): 167–72. doi:10.1016/0014-2999(82)90506-4. PMID 6290235.
3. Chou YC, Liao JF, Chang WY, Lin MF, Chen CF (March 1999). "Binding of dimemorfan to sigma-1 receptor and its anticonvulsant and locomotor effects in mice, compared with dextromethorphan and dextrorphan". Brain Research 821 (2): 516–9. doi:10.1016/S0006-8993(99)01125-7. PMID 10064839.
4. Gharagozlou, Parham; Hashemi, Ezzat; DeLorey, TimothyM; Clark, J David; Lameh, Jelveh (2006). "Pharmacological profiles of opioid ligands at Kappa opioid receptors". BMC Pharmacology 6 (1): 3. doi:10.1186/1471-2210-6-3. ISSN 1471-2210.
5. Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J (2006). "Pharmacological profiles of opioid ligands at Kappa opioid receptors". BMC Pharmacology 6 (1): 3. doi:10.1186/1471-2210-6-3. PMC 1403760. PMID 16433932.