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

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
Puqienine F, a novel veratramine alkaloid from the bulbs of Fritillaria puqiensis.	2006 May	16651778
Development of in vitro techniques for the important medicinal plant Veratrum californicum.	2006 Oct	17024590
[Determination of vetatramine in Veratrum nigrum by HPLC-ELSD].	2008 Apr	18589783
Hypotensive effect and toxicology of total alkaloids and veratramine from roots and rhizomes of Veratrum nigrum L. in spontaneously hypertensive rats.	2008 Aug	18771011
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
[Steroidal alkaloids of from Veratrum dahuricum].	2009 Dec	20222419
Synthesis of all diastereomers of the piperidine--alkaloid substructure of cyclopamine.	2009 Dec 3	19883099
Antitumor and antiplatelet activity of alkaloids from veratrum dahuricum.	2010 Jun	20013819
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
Hedgehog antagonist cyclopamine isomerizes to less potent forms when acidified.	2010 Sep 5	20236786

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.

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