Gemazocine

Gemazocine
Clinical data
ATC code	None;
Identifiers
	IUPAC name 10-(cyclopropylmethyl)-1-ethyl-13,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-ol;
CAS Number	54063-47-7;
PubChem CID	219096;
ChemSpider	189916;
UNII	V1A2S0LB62;
ChEMBL	ChEMBL2105066;
CompTox Dashboard (EPA)	DTXSID401023893 ;
Chemical and physical data
Formula	C20H29NO
Molar mass	299.458 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Oc1ccc4c(c1)C2(C(C(N(CC2)CC3CC3)C4)(C)C)CC;
	InChI InChI=1S/C20H29NO/c1-4-20-9-10-21(13-14-5-6-14)18(19(20,2)3)11-15-7-8-16(22)12-17(15)20/h7-8,12,14,18,22H,4-6,9-11,13H2,1-3H3; Key:AFZOCGNTFCGOEE-UHFFFAOYSA-N;

Gemazocine (R-15,497), also known as cyclogemine, is a non-selective opioid antagonist of the benzomorphan class.^[1]^[2]^[3] It may have partial agonist properties at some of the opioid receptors, such as at the kappa receptor (as it induces dysphoric effects in humans), but seems to be generally antagonistic in its actions.^[4]

References

^ Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 955. ISBN 978-0-412-46630-4. Retrieved 22 April 2012.
^ Gelders YG, de Ranter CJ, Schenk H (1979). "Structural Studies of Substituted 6,7-Benzomorphan Compounds. I. The Absolute Configuration of (−)-2-Cyclopropylmethyl-2'-hydroxy-5-ethyl-9,9-dimethyl-6,7-benzomorphan (Gemazocine) Hydrobromide". Acta Crystallographica B. 35 (3): 699–703. Bibcode:1979AcCrB..35..699G. doi:10.1107/S0567740879004477.
^ Verlinde C, De Ranter C (August 1988). "Assessment of the kappa-opioid activity of a series of 6,7-benzomorphans in the rabbit vas deferens". European Journal of Pharmacology. 153 (1): 83–87. doi:10.1016/0014-2999(88)90590-0. PMID 2850928.
^ Freye E, Hartung E, Schenk GK (May 1983). "Bremazocine: an opiate that induces sedation and analgesia without respiratory depression". Anesthesia and Analgesia. 62 (5): 483–488. doi:10.1213/00000539-198305000-00005. PMID 6301311.

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[Macdonald1997-1] Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 955. ISBN 978-0-412-46630-4. Retrieved 22 April 2012.

[Gelders1979-2] Gelders YG, de Ranter CJ, Schenk H (1979). "Structural Studies of Substituted 6,7-Benzomorphan Compounds. I. The Absolute Configuration of (−)-2-Cyclopropylmethyl-2'-hydroxy-5-ethyl-9,9-dimethyl-6,7-benzomorphan (Gemazocine) Hydrobromide". Acta Crystallographica B. 35 (3): 699–703. Bibcode:1979AcCrB..35..699G. doi:10.1107/S0567740879004477.

[pmid2850928-3] Verlinde C, De Ranter C (August 1988). "Assessment of the kappa-opioid activity of a series of 6,7-benzomorphans in the rabbit vas deferens". European Journal of Pharmacology. 153 (1): 83–87. doi:10.1016/0014-2999(88)90590-0. PMID 2850928.

[pmid6301311-4] Freye E, Hartung E, Schenk GK (May 1983). "Bremazocine: an opiate that induces sedation and analgesia without respiratory depression". Anesthesia and Analgesia. 62 (5): 483–488. doi:10.1213/00000539-198305000-00005. PMID 6301311.

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[2]

[3]

[4]

Clinical data

ATC code	None
Identifiers
IUPAC name 10-(cyclopropylmethyl)-1-ethyl-13,13-dimethyl-10-azatricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-4-ol
CAS Number	54063-47-7
PubChem CID	219096
ChemSpider	189916
UNII	V1A2S0LB62
ChEMBL	ChEMBL2105066
CompTox Dashboard (EPA)	DTXSID401023893
Chemical and physical data
Formula	C₂₀H₂₉NO
Molar mass	299.458 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Oc1ccc4c(c1)C2(C(C(N(CC2)CC3CC3)C4)(C)C)CC
InChI InChI=1S/C20H29NO/c1-4-20-9-10-21(13-14-5-6-14)18(19(20,2)3)11-15-7-8-16(22)12-17(15)20/h7-8,12,14,18,22H,4-6,9-11,13H2,1-3H3 Key:AFZOCGNTFCGOEE-UHFFFAOYSA-N