522-47-4

Basic information

• Product Name: LOCHNERINE
• Synonyms: LOCHNERINE;(+)-Lochenerine;10-Methoxysarpagan-17-ol;Lochenerine;10-Methoxynormacusine B;10-O-Methylsarpagine
• CAS NO: 522-47-4
• Molecular Formula: C₂₀H₂₄N₂O₂
• Molecular Weight: 324.422
• Mol File: 522-47-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 503.8°Cat760mmHg
• Flash Point: 258.5°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 5.68E-11mmHg at 25°C
• Refractive Index: 1.685
• CAS DataBase Reference: LOCHNERINE(CAS DataBase Reference)
• NIST Chemistry Reference: LOCHNERINE(522-47-4)
• EPA Substance Registry System: LOCHNERINE(522-47-4)

Safety Data

• Hazardous Substances Data: 522-47-4(Hazardous Substances Data)

Usage

Description

LOCHNERINE is a carboline alkaloid derived from Lochnera rosea and is also found in curare (Strychnos toxifera). It has been known by various names, including Alkaloid 'C' and C-Alkaloid T. LOCHNERINE exhibits optical activity with [α]D + 56° (pyridine) or + n° (EtOH) and forms a crystalline picrate with a double melting point of 177-9°C and 243-5°C (dec.). The methiodide of LOCHNERINE is identical to lochneram iodide, with a melting point of 235-8°C. A characteristic p-toluenesulphonyl derivative has been prepared, with a melting point of 153-4°C. The alkaloid contains one primary alcoholic hydroxyl group and yields the O-acetate as colorless needles, with a melting point of 243°C and [α]D 5.6° ± 3.0° (c 0.36, pyridine). The structure of LOCHNERINE is that of O-methylsarpagine.

Uses

1. Used in Pharmaceutical Industry:
LOCHNERINE is used as a pharmaceutical compound for its potential therapeutic applications. The expression is: LOCHNERINE is used as a pharmaceutical compound for its potential therapeutic applications.
2. Used in Research and Development:
LOCHNERINE is used as a research compound for studying its chemical properties, structure, and potential interactions with other molecules. The expression is: LOCHNERINE is used as a research compound for studying its chemical properties, structure, and potential interactions with other molecules.
3. Used in Drug Synthesis:
LOCHNERINE can be used as a starting material or intermediate in the synthesis of other pharmaceutical compounds. The expression is: LOCHNERINE is used as a starting material or intermediate in the synthesis of other pharmaceutical compounds.
4. Used in Toxicological Studies:
Due to its presence in curare, LOCHNERINE can be used in toxicological studies to understand its effects on the nervous system and potential applications in the development of neuromuscular blocking agents. The expression is: LOCHNERINE is used in toxicological studies to understand its effects on the nervous system and potential applications in the development of neuromuscular blocking agents.
5. Used in Traditional Medicine:
LOCHNERINE may have potential applications in traditional medicine, where it could be used for its various pharmacological properties. The expression is: LOCHNERINE is used in traditional medicine for its various pharmacological properties.

References

Janot, LeMen., Cornpt. rend., 243, 1789 (1956) Mors et at., Chern. Ind., 173 (1956) Arnold et at., Helv. Chirn. Acta, 40, 705 (1957) Arnold et al., ibid, 41, 1505 (1958) Karrer et at., Angew. Chern., 70,644 (1958)

InChI:InChI=1/C20H24N2O2/c1-3-11-9-22-18-8-15-14-6-12(24-2)4-5-17(14)21-20(15)19(22)7-13(11)16(18)10-23/h3-6,13,16,18-19,21,23H,7-10H2,1-2H3/b11-3-/t13-,16+,18-,19-/m0/s1

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Downstream Products

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Relevant articles and documents

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Stereospecific approach to the synthesis of ring-A oxygenated sarpagine indole alkaloids. Total synthesis of the dimeric indole alkaloid P -(+)-dispegatrine and six other monomeric indole alkaloids

The first regio- and stereocontrolled total synthesis of the bisphenolic, bisquaternary alkaloid (+)-dispegatrine (1) has been accomplished in an overall yield of 8.3% (12 reaction vessels) from 5-methoxy-d-tryptophan ethyl ester (17). A crucial late-stage thallium(III) mediated intermolecular oxidative dehydrodimerization was employed in the formation of the C9-C9′ biaryl axis in 1. The complete stereocontrol observed in this key biaryl coupling step is due to the asymmetric induction by the natural sarpagine configuration of the monomer lochnerine (6) and was confirmed by both the Suzuki and the oxidative dehydrodimerization model studies on the tetrahydro β-carboline (35). The axial chirality of the lochnerine dimer (40) and in turn dispegatrine (1) was established by X-ray crystallography and was determined to be P(S). Additionally, the first total synthesis of the monomeric indole alkaloids (+)-spegatrine (2), (+)-10-methoxyvellosimine (5), (+)-lochnerine (6), lochvinerine (7), (+)-sarpagine (8), and (+)-lochneram (11) were also achieved via the common pentacyclic intermediate 16.