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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H39NO2
Molecular Weight 409.6041
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VERATRAMINE

SMILES

C[C@H]([C@@H]1NC[C@@H](C)C[C@H]1O)C2=C(C)C3=C(C=C2)[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4C3

InChI

InChIKey=MALFODICFSIXPO-KFKQDBFTSA-N
InChI=1S/C27H39NO2/c1-15-11-25(30)26(28-14-15)17(3)20-7-8-21-22-6-5-18-12-19(29)9-10-27(18,4)24(22)13-23(21)16(20)2/h5,7-8,15,17,19,22,24-26,28-30H,6,9-14H2,1-4H3/t15-,17-,19-,22-,24-,25+,26-,27-/m0/s1

HIDE SMILES / InChI

Molecular Formula C27H39NO2
Molecular Weight 409.6041
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Veratramine, a steroidal alkaloid originating from Veratrum nigrum L. CYP2D6 and SULT2A1 mediating hydroxylation and sulfation were identified as the major biotransformation for veratramine. Veratramine significantly inhibits the hedgehog pathway in NIH/3T3 cells. Veratramine is both a release and uptake inhibitor of serotonin. Veratramine exhibits cytotoxic activity against human tumor cell lines A549, PANC-1, SW1990 and NCI-H249. Veratramine has demonstrated distinct anti-hypertension effects in spontaneously hypertensive rats.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.25 µM [Ki]
33.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
0.56 to 2.24 mg/kg
Route of Administration: Oral
In Vitro Use Guide
The uptake of 3H-5-HT into the frontal cortical slices was inhibited by veratramine in a concentration-dependent fashion with an IC50 of 0.13 uM.
Substance Class Chemical
Record UNII
RK363YG315
Record Status Validated (UNII)
Record Version