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Details

Stereochemistry RACEMIC
Molecular Formula C16H25NS.ClH
Molecular Weight 299.902
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GACYCLIDINE HYDROCHLORIDE

SMILES

Cl.C[C@H]1CCCC[C@]1(N2CCCCC2)C3=CC=CS3

InChI

InChIKey=AJPKYPDCAXFLDK-KUARMEPBSA-N
InChI=1S/C16H25NS.ClH/c1-14-8-3-4-10-16(14,15-9-7-13-18-15)17-11-5-2-6-12-17;/h7,9,13-14H,2-6,8,10-12H2,1H3;1H/t14-,16+;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H25NS
Molecular Weight 263.441
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Gacyclidine (GK11) is a derivative of phencyclidine with neuroprotective properties. Tritiated gacyclidine and its enantiomers bind to NMDA receptors with binding parameters similar to those of other non‐competitive NMDA receptor antagonists. Beneficial effects of gacyclidine include reduction of lesion size and improvement of functional parameters after injury. In traumatic brain injury models, gacyclidine also improves behavioral parameters and neuronal survival. In an animal model of Amyotrophic lateral sclerosis (ALS), functional alteration of locomotor activity was evident and improved the survival of mice, suggesting that chronic administration of gacyclidine beginning at early symptomatic stage may be beneficial for patients with ALS. Gacyclidine has also been associated with altered mental status and end organ damage in patients.

Approval Year

Substance Class Chemical
Created
by admin
on Sat Dec 16 06:31:50 GMT 2023
Edited
by admin
on Sat Dec 16 06:31:50 GMT 2023
Record UNII
34562OW80C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GACYCLIDINE HYDROCHLORIDE
WHO-DD  
Common Name English
PIPERIDINE, 1-((1R,2S)-2-METHYL-1-(2-THIENYL)CYCLOHEXYL)-, HYDROCHLORIDE, REL-
Common Name English
GACYCLIDINE HYDROCHLORIDE, (±)-
Common Name English
Gacyclidine hydrochloride [WHO-DD]
Common Name English
PIPERIDINE, 1-((1R,2S)-2-METHYL-1-(2-THIENYL)CYCLOHEXYL)-, HYDROCHLORIDE (1:1), REL-
Common Name English
(±)-GACYCLIDINE HYDROCHLORIDE
Common Name English
PIPERIDINE, 1-(2-METHYL-1-(2-THIENYL)CYCLOHEXYL)-, HYDROCHLORIDE, CIS-
Common Name English
Code System Code Type Description
PUBCHEM
67111961
Created by admin on Sat Dec 16 06:31:50 GMT 2023 , Edited by admin on Sat Dec 16 06:31:50 GMT 2023
PRIMARY
FDA UNII
34562OW80C
Created by admin on Sat Dec 16 06:31:50 GMT 2023 , Edited by admin on Sat Dec 16 06:31:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID40157204
Created by admin on Sat Dec 16 06:31:50 GMT 2023 , Edited by admin on Sat Dec 16 06:31:50 GMT 2023
PRIMARY
CAS
131774-33-9
Created by admin on Sat Dec 16 06:31:50 GMT 2023 , Edited by admin on Sat Dec 16 06:31:50 GMT 2023
PRIMARY
SMS_ID
100000087236
Created by admin on Sat Dec 16 06:31:50 GMT 2023 , Edited by admin on Sat Dec 16 06:31:50 GMT 2023
PRIMARY
EVMPD
SUB02296MIG
Created by admin on Sat Dec 16 06:31:50 GMT 2023 , Edited by admin on Sat Dec 16 06:31:50 GMT 2023
PRIMARY
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