STRYCHNINE

Base Information

• Chemical Name: STRYCHNINE
• CAS No.: 57-24-9
• Molecular Formula: C21H22 N2 O2
• Molecular Weight: 334.418
• Hs Code.: 29349990
• NSC Number: 5365
• Wikidata: Q104667372
• Metabolomics Workbench ID: 123710
• ChEMBL ID: CHEMBL1609139
• Mol file: 57-24-9.mol

Synonyms:Strychnine(8CI);4,6-Methano-6H,14H-indolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline,strychnidin-10-one deriv.; (-)-Strychnine; Certox; NSC 5365; Strychnin

Chemical Property of STRYCHNINE

Chemical Property:

• Appearance/Colour: white crystals or powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 284-286 °C(lit.)
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 559.9°Cat760mmHg
• PKA: 8.26(at 25℃)
• Flash Point: 292.4°C
• PSA: 32.78000
• Density: 1.42g/cm³
• LogP: 2.09540
• Storage Temp.: Poison room
• Solubility.: chloroform: clear to hazy
• Water Solubility.: 143 mg l-1
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 334.168127949
• Heavy Atom Count: 25
• Complexity: 689

Purity/Quality:

Strychnine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+,N
• Statements: 27/28-50/53
• Safety Statements: 36/37-45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN2CC3=CCOC4CC(=O)N5C6C4C3CC2C61C7=CC=CC=C75
• Description: Strychnine, C21H22N2O2, Mr 334.4, mp 270–280 ?C (decomp.), forms colorless crystals which are slightly soluble in water, moderately in benzene, ethanol, readily soluble in chloroform [9, p. 1121].
• Physical properties: Colorless to white, odorless crystals. Bitter taste.
• Uses: Strychnine as nux vomica was available in apothecaries throughoutthe 19th century, and strychnine salts such as strychnine sulfate, strychnine nitrate, andstrychnine phosphate were a popular medicine. It was sold as pills, powders, and tinctures.Small quantities of strychnine were added to tonics to serve as stimulants. Because its bittertaste stimulates saliva and gastric production, strychnine was used to counteract the lossof appetite produced by various diseases. Hypodermic injections of strychnine along withdigitalis were prescribed for treating acute heart failure in the early 20th century. Otherconditions for which strychnine was prescribed included paralysis, impotence, alcoholism,and drug addiction.Today strychnine as nux vomica is still available as an herbal ingredient for herbal and homeopathic remedies. The action of nux vomica is attributed to strychnine and brucine. It is recommended for stomach ailments such as atonic dyspepsia, constipation, heart burn, and indigestion. It is reported to relieve nausea during pregnancy. Chinese herbalists use nux vomica externally to treat tumors, headaches, and paralysis. It is recommended for the treatment of Bell's palsy. Strychnine has some uses in modern traditional medicine. It has been used to treat the genetic disorder nonketotic hyperglycinaemia (NKH). NKH is related to glycine metabolism; it can lead to high levels of the inhibitory receptor glycine resulting in seizures. Strychnine is used in neurological research by applying it to areas of the brain or spinal column and observing how the nervous system responds. This method is called strychnine neuronography. Strychnine has been used in conjunction with antivenoms to treat poisonous snake bites. Strychnine is sometimes cut into cocaine, heroin, and other illegal substances in the production of designer drugs. Strychnine was once used liberally as a pesticide, especially to control vertebrates.It is used as a salt in granular bait formulations. In the United States its use has been progressively limited over the years. . In the1980s, its use was curtailed for above-ground applications to reduce toxicity to nontargetspecies, especially birds; by the end of the decade, its use was limited to below ground.Currently, strychnine is only registered for use by the EPA as a below-ground bait pesticidefor use on pocket gophers. Strychnine occurs in the seeds of strychnosspecies (S. nux vomica L., S. Loganiaceae,and S. ignatii Berg). The total alkaloid con tent in these plants is 2–3%. The composition of strychnine in these species rangesbetween 1% and 3%. Strychnine is widelyknown as a poison. Its therapeutic applica tions are very limited. It is used as a rodentpoison. Strychnine is used for the control of moles, squirrels, rabbits, gophers, mice and other small rodents and of bird pests. Rats normally avoid the bait. Destroying rodents and predatory animals.
• Indications: Strychnine is clinically used for the treatment of barbiturate poisoning, hemiplegia, amblyopia, blood diseases, and streptomycin toxicity. Strychnine is used to treat aplastic anemia.
• Clinical Use: Strychnine is commonly used in the treatment of flaccid paralysis, ENT diseases, diabetes, neurasthenia, acute myelitis, peripheral neuritis, and aplastic anemia in clinic. However, due to the relatively high toxicity of strychnine, excessive or longterm use of strychnine may lead to poison. Studies have shown that the combination of Strychnos and Glycyrrhiza or cinnamon can reduce the toxicity of strychnine. Therefore, further study of poisoning mechanism and toxicokinetics of strychnine is of great significance for the clinical safety

Technology Process of STRYCHNINE

There total 98 articles about STRYCHNINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

(-)-Wieland-Gumlich aldehyde (724794-46-1) + malonic acid (141-82-2) → strychnidin-10-one (57-24-9)

Guidance literature:

With sodium acetate; acetic anhydride; In acetic acid; at 120 ℃;

DOI:10.1038/nature10232

Reference yield: 65.0%

malonic acid (141-82-2) + (17R,19E)-17,18-epoxy-cur-19-en-17-ol (466-85-3) → strychnidin-10-one (57-24-9)

Guidance literature:

With sodium acetate; acetic anhydride; acetic acid; at 110 ℃;

DOI:10.1021/ja00073a057

Reference yield: 16.0%

(+)-isostrychnine (467-16-3) → strychnidin-10-one (57-24-9)

Guidance literature:

With potassium hydroxide; In ethanol; at 85 ℃; for 6h;

DOI:10.1021/ja029382u

upstream raw materials:

19α-oxy-strychnidin-10-one

glycerol

formic acid

icajine

Downstream raw materials:

(R)-2-methyl-2-(3,4-dichlorophenoxy)acetic acid

(R)-2-methylglutaric acid

(S)-2-methylglutaric acid

L-2-(2,4-dichloro-phenoxy)-butyric acid

Refernces

• 1、 Jones, Spencer B.,Simmons, Bryon,Mastracchio, Anthony,MacMillan, David W. C.. "Collective synthesis of natural products by means of organocascade catalysis". scheme or table. p. 183 - 188. Retrieved 2012/05/20.
• 2、 Ohshima, Takashi,Xu, Youjun,Takita, Ryo,Shibasaki, Masakatsu. "Enantioselective total synthesis of (-)-strychnine: Development of a highly practical catalytic asymmetric carbon-carbon bond formation and domino cyclization". . p. 9569 - 9588. Retrieved 2007/10/03.