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Details

Stereochemistry ACHIRAL
Molecular Formula C11H13N3O
Molecular Weight 203.2404
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 5-CARBOXAMIDOTRYPTAMINE

SMILES

NCCC1=CNC2=C1C=C(C=C2)C(N)=O

InChI

InChIKey=WKZLNEWVIAGNAW-UHFFFAOYSA-N
InChI=1S/C11H13N3O/c12-4-3-8-6-14-10-2-1-7(11(13)15)5-9(8)10/h1-2,5-6,14H,3-4,12H2,(H2,13,15)

HIDE SMILES / InChI

Molecular Formula C11H13N3O
Molecular Weight 203.2404
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

5-carboxamidotryptamine (5-CT) is a 5-HT1 agonist with high affinity at 5-HT1A, 5-HT1B, 5-HT1D, 5-HT5 and 5-HT7 receptors. As one of the first compounds reported active at 5-HT1B, 5-carboxamidotryptamine was originally investigated as a potential treatment for migraine. During preclinical studies, 5-CT was found to cause vasodilatation of carotid circulation and hypotension in animals, effects that were later attributed to potent agonist activity at 5-HT7. Subsequent structural modifications of 5-CT led to the discovery of the anti-migraine drug sumatriptan. 5-CT is primarily used as a pharmacological tool for study of 5-HT1 and 5-HT7 mediated functional responses.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.3 nM [Ki]
0.029 nM [Ki]
7.7 nM [Ki]
8.9 null [pKi]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Rats: 5-carboxamidotryptamine (5-CT) above the dosage of 0.05 mg/kg elicited significant hyperglycemic effects and 0.1 mg/kg, induced a 35% increase in plasma glucose levels.
Route of Administration: Intraperitoneal
In Vitro Use Guide
5-carboxamidotryptamine (5-CT; 0.3 uM) inhibited electrical field stimulation (EFS)-induced contractions of dog antrum longitudinal muscle in vitro.
Substance Class Chemical
Record UNII
91H76044O0
Record Status Validated (UNII)
Record Version