Veracevine

{{Infobox chemical | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477002123 | ImageFile = Veracevine.png | ImageSize = 200px | ImageAlt = | IUPACName = (3β,5α,12β,20R)-3,12,20-trihydroxy-5,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-one | OtherNames = | Section1 = ! colspan=2 style="background: #f8eaba; text-align: center;" |Identifiers

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Veracevine
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ChemSpider ID	[[ChemSpiderID|]]
Molecular Formula	[[Molecular formula|]]
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Density	g/cm3
Melting Point	°C
Boiling Point	°C
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Veracevine
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InChI

• InChI=1S/C27H43NO3/c1-16-5-6-17-15-19-18-7-8-20-21(30)9-11-27(20,4)25(18)23(29)13-14-26(19,3)24(17)22(28)10-12-16/h10,12,18-25,29-30H,5-9,11,13-15H2,1-4H3/t18-,19-,20-,21-,22-,23-,24-,25-,26-,27-/m0/s1

  Key: ZQZKQJXKJZQKJX-UHFFFAOYSA-N

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SMILES

• C[C@H]1CC[C@@H]2[C@@H]3CC[C@H]4[C@@H]5CC[C@H](C[C@H]5CC[C@]4(C3=O)C2=C1)O

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Veracevine is a naturally occurring alkaloid found in certain species of the Veratrum genus, particularly in Veratrum album and Veratrum viride. It is a member of the steroidal alkaloid family and is known for its potent biological activity.

Structure and Properties

Veracevine is a complex steroidal alkaloid with a molecular formula of C₂₇H₄₃NO₃. It features a polycyclic structure typical of steroidal compounds, with multiple hydroxyl groups contributing to its chemical reactivity and solubility in organic solvents. The compound is a white crystalline solid with a melting point of 240-242 °C.

Biosynthesis

Veracevine is biosynthesized in plants through the mevalonate pathway, which is responsible for the production of terpenoids and steroids. The biosynthesis involves the cyclization of squalene to form the steroidal backbone, followed by a series of hydroxylation and oxidation reactions that introduce the functional groups characteristic of veracevine.

Biological Activity

Veracevine exhibits significant biological activity, primarily due to its interaction with ion channels and receptors in the nervous system. It is known to affect sodium channels, leading to altered nerve impulse transmission. This activity underlies its toxic effects, which can include cardiotoxicity and neurotoxicity.

Toxicology

The toxicity of veracevine is a major concern, particularly in cases of accidental ingestion of plants containing the alkaloid. Symptoms of veracevine poisoning include nausea, vomiting, hypotension, bradycardia, and in severe cases, respiratory failure. Treatment is primarily supportive, with a focus on maintaining cardiovascular and respiratory function.

Uses

While veracevine itself is not used therapeutically due to its toxicity, research into its mechanism of action has provided insights into the development of new pharmacological agents. The study of veracevine and related alkaloids has contributed to the understanding of ion channel modulation and its potential therapeutic applications.

Also see

• Veratrum
• Steroidal alkaloid
• Ion channel
• Cardiotoxicity