Veratramine
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MedKoo CAT#: 571541

CAS#: 60-70-8

Description: Veratramine is a hypotensive alkaloid isolated from the rhizomes of Veratrum. Veratramine modulates AP-1-dependent gene transcription by directly binding to programmable DNA. Veratramine, as a potent natural modulator of AP-1, selectively binds to a specific site (TRE 5'-TGACTCA-3') of the AP-1 target DNA sequence and regulates AP-1-dependent gene transcription without interfering with cystosolic signaling cascades that might lead to AP-1 activation.


Chemical Structure

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Veratramine
CAS# 60-70-8

Theoretical Analysis

MedKoo Cat#: 571541
Name: Veratramine
CAS#: 60-70-8
Chemical Formula: C27H39NO2
Exact Mass: 409.2981
Molecular Weight: 409.61
Elemental Analysis: C, 79.17; H, 9.60; N, 3.42; O, 7.81

Price and Availability

Size Price Availability Quantity
10.0mg USD 240.0 2 Weeks
50.0mg USD 450.0 2 Weeks
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Synonym: Veratramine; NSC 17821; NSC17821; NSC-17821; NSC 23880; NSC-23880; NSC23880.

IUPAC/Chemical Name: (3beta,23beta)-14,15,16,17-Tetradehydroveratraman-3,23-diol

InChi Key: MALFODICFSIXPO-KFKQDBFTSA-N

InChi Code: 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

SMILES Code: C[C@H]([C@H]1[C@H](O)C[C@H](C)CN1)C2=CC=C3[C@]4([H])CC=C5C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC3=C2C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 409.61 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Bai F, Liu K, Li H, Wang J, Zhu J, Hao P, Zhu L, Zhang S, Shan L, Ma W, Bode AM, Zhang W, Li H, Dong Z. Veratramine modulates AP-1-dependent gene transcription by directly binding to programmable DNA. Nucleic Acids Res. 2018 Jan 25;46(2):546-557. doi: 10.1093/nar/gkx1241. PubMed PMID: 29237043; PubMed Central PMCID: PMC5778533.

2: Cong Y, Zhang JL, Li SS, Shen S, Wang JY, Cai Z. Pharmacokinetics and metabolism study of veratramine in mice after oral administration using LC-MS/MS. Biomed Chromatogr. 2016 Sep;30(9):1515-22. doi: 10.1002/bmc.3717. Epub 2016 Apr 3. PubMed PMID: 26972867.

3: Lyu C, Zhang Y, Zhou W, Zhang S, Kou F, Wei H, Zhang N, Zuo Z. Gender-Dependent Pharmacokinetics of Veratramine in Rats: In Vivo and In Vitro Evidence. AAPS J. 2016 Mar;18(2):432-44. doi: 10.1208/s12248-016-9870-9. Epub 2016 Jan 20. PubMed PMID: 26791530; PubMed Central PMCID: PMC4779099.

4: Lyu C, Zhou W, Zhang Y, Zhang S, Kou F, Wei H, Zhang N, Zuo Z. Identification and characterization of in vitro and in vivo metabolites of steroidal alkaloid veratramine. Biopharm Drug Dispos. 2015 Jul;36(5):308-24. doi: 10.1002/bdd.1942. Epub 2015 Apr 21. PubMed PMID: 25765359.

5: Cong Y, Guo J, Tang Z, Lin S, Zhang Q, Li J, Cai Z. Metabolism Study of Veratramine Associated with Neurotoxicity by Using HPLC-MSn. J Chromatogr Sci. 2015 Aug;53(7):1092-9. doi: 10.1093/chromsci/bmu171. Epub 2014 Dec 29. PubMed PMID: 25547283.

6: Wang L, Li W, Liu Y. Hypotensive effect and toxicology of total alkaloids and veratramine from roots and rhizomes of Veratrum nigrum L. in spontaneously hypertensive rats. Pharmazie. 2008 Aug;63(8):606-10. PubMed PMID: 18771011.

7: Zhang S, Zhou J, Shou Q, Peng Y, Shen Z. [Determination of jervine and veratramine in Veratrum plants using high performance liquid chromatography coupled with evaporative light scattering detection]. Se Pu. 2008 Jan;26(1):56-9. Chinese. PubMed PMID: 18438025.

8: Li HJ, Jiang Y, Li P, Ye WC. Puqienine F, a novel veratramine alkaloid from the bulbs of Fritillaria puqiensis. Chem Pharm Bull (Tokyo). 2006 May;54(5):722-4. PubMed PMID: 16651778.

9: Thron CD, McCann FV. Pharmacological tests of the mechanism of the periodic rhythm caused by veratramine in the sinoatrial node of the guinea pig. Gen Pharmacol. 1999 Jan;32(1):81-9. PubMed PMID: 9888259.

10: Thron CD, McCann FV. Studies on the bradycardia and periodic rhythm caused by veratramine in the sinoatrial node of the guinea pig. J Electrocardiol. 1998 Jul;31(3):257-68. PubMed PMID: 9682902.

11: el Sayed KA. Microbial biotransformation of veratramine. J Nat Prod. 1998 Jan;61(1):149-51. PubMed PMID: 9461666.

12: Badria FA, McChesney JD, Halim AF, Zaghloul AM, el Sayed KA. Time course and inhibition of stavaroside K, veratramine and cevine-induced hemolysis by other pregnane glycosides and Veratrum alkaloids. Pharmazie. 1995 Jun;50(6):421-3. PubMed PMID: 7651981.

13: Nagata R, Izumi K, Iwata S, Shimizu T, Fukuda T. Mechanisms of veratramine-induced 5-HT syndrome in mice. Jpn J Pharmacol. 1991 Jan;55(1):139-46. PubMed PMID: 1710298.

14: Nagata R, Izumi K. Veratramine-induced behavior associated with serotonergic hyperfunction in mice. Jpn J Pharmacol. 1991 Jan;55(1):129-37. PubMed PMID: 1710297.

15: Fukuda T. [Veratramine-induced myoclonus]. Seishin Shinkeigaku Zasshi. 1990;92(11):865-9. Japanese. PubMed PMID: 2087534.

16: Sures HA, Innes IR. Isolation of the sino-atrial node with veratramine. J Pharmacol Exp Ther. 1979 Jul;210(1):116-9. PubMed PMID: 448639.

17: Izumi K, Butterworth RF, Tunnicliff G, Gonce M, Barbeau A. Possible serotonin-agonist action of veratramine. Brain Res Bull. 1978 May-Jun;3(3):237-10. PubMed PMID: 213177.

18: Koga T, Fukuda T, Suenaga N. Proceedings: Relationship between struggling movement induced by veratramine and brain monoamines. Jpn J Pharmacol. 1974;24(0):s:63. PubMed PMID: 4545618.

19: Simaan J, Fawaz G. The metabolic effect of noradrenaline on the isolated canine heart after blockade of the chronotropic action by veratramine. Naunyn Schmiedebergs Arch Pharmacol. 1973;277(2):199-209. PubMed PMID: 4267318.

20: Mitsuhashi H, Shibata K. Studies on C-nor-d-homosteroids. VII. Synthesis of nitrogen-free veratramine derivatives. Chem Pharm Bull (Tokyo). 1968 May;16(5):814-8. PubMed PMID: 5728170.