Ketazocine

Ketazocine
Clinical data
Routes of; administration	Oral
ATC code	none;
Identifiers
	IUPAC name (2S,6R,11R)-3-(cyclopropylmethyl)-8-hydroxy-6,11-dimethyl-3,4,5,6-tetrahydro-2,6-methano-3-benzazocin-1(2H)-one;
CAS Number	36292-69-0 ;
PubChem CID	3054741;
ChemSpider	2316328 ;
UNII	6IO4IG518S;
KEGG	D04649 ;
CompTox Dashboard (EPA)	DTXSID10897529 ;
Chemical and physical data
Formula	C18H23NO2
Molar mass	285.387 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2c1c(cc(O)cc1)[C@]3([C@H]([C@@H]2N(CC3)CC4CC4)C)C;
	InChI InChI=1S/C18H23NO2/c1-11-16-17(21)14-6-5-13(20)9-15(14)18(11,2)7-8-19(16)10-12-3-4-12/h5-6,9,11-12,16,20H,3-4,7-8,10H2,1-2H3/t11-,16-,18+/m0/s1 ; Key:HQBZLVPZOGIAIQ-SDDDUWNISA-N ;
	(verify)

Ketazocine (INN), also known as ketocyclazocine, is a benzomorphan derivative used in opioid receptor research. Ketocyclazocine is an exogenous opioid that binds to the κ opioid receptor.^[1]

Activation of this receptor is known to cause sleepiness, a decrease in pain sensation and (potentially) dysphoria, paranoia, and hallucinations. It also causes an increase in urine production because it inhibits the release of vasopressin. (Vasopressin is an endogenous substance that assists in regulating fluid and electrolyte balance in the body and decreases the amount of water released into the urine.)

Unlike other opioids, substances that only bind to the κ receptor theoretically do not depress the respiratory system.

The crystal structure of Ketazocine was determined in 1983.^[2]

References

^ Leander JD (September 1982). "Effects of ketazocine, ethylketazocine and phenazocine on schedule-controlled behavior: antagonism by naloxone". Neuropharmacology. 21 (9): 923–8. doi:10.1016/0028-3908(82)90085-5. PMID 6128693.
^ Verlinde CL, De Ranter CJ. "(1S, 5R, 9R)-2-Cyclopropylmethyl-2'-hydroxy-5, 9-dimethyl-8-oxo-6, 7-benzomorphan hydrochloride monohydrate (ketazocine), C18H23NO2. HCl. H2O". Acta Crystallogr. C. 39: 1703–1706.

[1] Leander JD (September 1982). "Effects of ketazocine, ethylketazocine and phenazocine on schedule-controlled behavior: antagonism by naloxone". Neuropharmacology. 21 (9): 923–8. doi:10.1016/0028-3908(82)90085-5. PMID 6128693.

[2] Verlinde CL, De Ranter CJ. "(1S, 5R, 9R)-2-Cyclopropylmethyl-2'-hydroxy-5, 9-dimethyl-8-oxo-6, 7-benzomorphan hydrochloride monohydrate (ketazocine), C18H23NO2. HCl. H2O". Acta Crystallogr. C. 39: 1703–1706.

[1]

[2]

Clinical data

Routes of administration	Oral
ATC code	none
Identifiers
IUPAC name (2S,6R,11R)-3-(cyclopropylmethyl)-8-hydroxy-6,11-dimethyl-3,4,5,6-tetrahydro-2,6-methano-3-benzazocin-1(2H)-one
CAS Number	36292-69-0
PubChem CID	3054741
ChemSpider	2316328
UNII	6IO4IG518S
KEGG	D04649
CompTox Dashboard (EPA)	DTXSID10897529
Chemical and physical data
Formula	C₁₈H₂₃NO₂
Molar mass	285.387 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C2c1c(cc(O)cc1)[C@]3([C@H]([C@@H]2N(CC3)CC4CC4)C)C
InChI InChI=1S/C18H23NO2/c1-11-16-17(21)14-6-5-13(20)9-15(14)18(11,2)7-8-19(16)10-12-3-4-12/h5-6,9,11-12,16,20H,3-4,7-8,10H2,1-2H3/t11-,16-,18+/m0/s1 Key:HQBZLVPZOGIAIQ-SDDDUWNISA-N
(verify)

Ketazocine

See also

References