VERATRAMINE

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 Search

SMILES

[H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC4=C2C=CC([C@H](C)[C@]5([H])NC[C@@H](C)C[C@H]5O)=C4C

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25765359 | https://www.ncbi.nlm.nih.gov/pubmed/20013819 | https://www.ncbi.nlm.nih.gov/pubmed/18570211 | https://www.ncbi.nlm.nih.gov/pubmed/18771011 | https://www.ncbi.nlm.nih.gov/pubmed/1710298

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 Target	Pharmacology	Potency
serotonin secretion 8 Target ID: GO:0001820 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1710298	Inhibitor 8297
serotonin uptake 20 Target ID: GO:0051610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1710298	Inhibitor 8297	0.25 µM [Ki]
Cytochrome P450 2D6 61 Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25765359	Substrate 661	33.0 µM [Ki]
Alcohol sulfotransferase 2 Target ID: CHEMBL2077 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25765359	Substrate 661
Hedgehog signaling pathway 11 Target ID: map04340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20013819	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18771011	Primary		Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18570211 https://www.ncbi.nlm.nih.gov/pubmed/20013819	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Determination of vetatramine in Veratrum nigrum by HPLC-ELSD].	2008 Apr	18589783
Antitumor activity of extracts and compounds from the rhizomes of Veratrum dahuricum.	2008 Aug	18570211
[Determination of jervine and veratramine in Veratrum plants using high performance liquid chromatography coupled with evaporative light scattering detection].	2008 Jan	18438025
Isolation, purification, and full NMR assignments of cyclopamine from Veratrum californicum.	2008 Jun 24	18577213
Synthesis of all diastereomers of the piperidine--alkaloid substructure of cyclopamine.	2009 Dec 3	19883099
Characterization and identification of steroidal alkaloids in Fritillaria species using liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry.	2010 Nov 5	20926090

Patents

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 Created by `admin` on `Sat Dec 16 10:47:49 GMT 2023` Edited by `admin` on `Sat Dec 16 10:47:49 GMT 2023`
Record UNII	RK363YG315
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

VERATRAMINE

Common Name

English

VERATRAMINE [MI]

Common Name

English

NSC-17821

Code

English

NSC-23880

Code

English

3-PIPERIDINOL, 5-METHYL-2-((1S)-1-((3S,6AR,11AS,11BR)-2,3,4,6,6A,11,11A,11B-OCTAHYDRO-3-HYDROXY-10,11B-DIMETHYL-1H-BENZO(A)FLUOREN-9-YL)ETHYL)-, (2S,3R,5S)-

Systematic Name

English

Code System Code Type Description

NSC

23880