Pharmakon1600-01504027

Base Information

• Chemical Name: Pharmakon1600-01504027
• CAS No.: 485-35-8
• Molecular Formula: C11H14N2O
• Molecular Weight: 190.245
• Hs Code.: 29399990
• NSC Number: 758665
• Wikidata: Q27166989
• Mol file: 485-35-8.mol

Synonyms:Spectrum_001465;SpecPlus_000618;Spectrum2_000470;Spectrum3_001611;Spectrum4_001834;Spectrum5_000627;BSPBio_003241;KBioGR_002534;KBioSS_001945;DivK1c_006714;SPECTRUM1504027;SPBio_000580;SCHEMBL8309064;CHEBI:95183;KBio1_001658;KBio2_001945;KBio2_004513;KBio2_007081;KBio3_002461;HMS1922B03;Pharmakon1600-01504027;LSM-6464;CCG-39978;NSC758665;NSC-758665;SDCCGMLS-0066826.P001;NCGC00178191-01;VU0243453-3;BRD-A55579717-001-02-4;BRD-A55579717-001-03-2;Q27166989

Chemical Property of Pharmakon1600-01504027

Chemical Property:

• Appearance/Colour: Off-white to tan crystalline solid
• Vapor Pressure: 4.95E-07mmHg at 25°C
• Melting Point: 154-156 °C(lit.)
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 413 °C at 760 mmHg
• PKA: 6.11, 13.08(at 25℃)
• Flash Point: 203.6 °C
• PSA: 34.03000
• Density: 1.24 g/cm³
• LogP: 0.88380
• Storage Temp.: Store at RT
• Solubility.: 439g/l
• Water Solubility.: 439g/L(16 oC)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 190.110613074
• Heavy Atom Count: 14
• Complexity: 332

Purity/Quality:

99% ^*data from raw suppliers

Cytisine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-28-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CNCC1C3=CC=CC(=O)N3C2
• Isomeric SMILES: C1[C@@H]2CNCC1C3=CC=CC(=O)N3C2
• Description: Cytisine (also known as baptitoxine and sophorine) is a kind of naturally occurring alkaloid that can be found in several plant genera including Laburnum and Cytisus in the family Fabaceae. It has been shown that it is effective in the smoking cessation treatment. It is a low efficacy partial agonist of alpha4-beta2 nicotinic acetylcholine receptors, which is the central target of the nicotine that facilitates addiction. Cytisine is capable of reducing the effect of nicotine on dopamine release on the mesolimbic system as well as attenuating the nicotine withdrawal symptoms. Cytisine is also a useful reagent for organic chemistry such as being used for the manufacture of sparteine surrogate. It is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus of the family Fabaceae. Pi-Zhen-Ye-Huang-Hua (Thermopsis lanceolata R.Br) contains large amount of cytisine, and it is distributed in the northeast, north, and northwest of China. This herb has been traditionally used for treating cough in China and was recorded in “Yue-Wang-Yao-Zhen,”“Jing-ZhuBen-Cao,”“Zhong-Hua-Ben-Cao,” and “Ning-Xia-Zhong-Cao-Yao-Shou-Ce.”
• Biological Functions: Cytisine has a physiological action similar to that of nicotine. Poisoning in Europe is generally from laburnum trees (Laburnum anagyroides, Leguminosae), while, in the tropics and America, Sophora species (Leguminosae) are often the cause. The alkaloid occurs in all parts of laburnum, but is most concentrated in the seeds, which can be mistaken for peas by children. Cytisine does not always affect cattle, but this compound can be excreted in milk and so poison children.
• Physical properties: Appearance: white or yellow powder. Solubility: soluble in water, pyridine, acetone, ethanol, and methanol and only slightly soluble in benzene but insoluble in petroleum ether. Melting point: 154–156?°C. Specific optical rotation: ?114.0 to ?116.0° (C?=?0.1, H2O). Toxic, stable under room temperature, and should be kept in a dry and dark place.
• Uses: antiinflammatory, respiratory stimulant Toxic priniciple in seed of Laburnum anagyroides and other Leguminosae. A neuronal nicotinic acetylcholine agonist. Toxic priniciple in seed of Laburnum anagyroides and other Leguminosae. A neuronal nicotinic acetylcholine agonist. Cytisine occurs in the seeds of Cytisus labur num L. and other Leguminosae.
• Indications: It is the first effective medicine in the world for smoking cessation, which does not contain nicotine and antidepressants. It is administered perorally according to the following schedule:First 3 days: one tablet six times daily (every 2 h) with a parallel reduction of the number of cigarettes smoked.If the result is unsatisfactory, the treatment is discontinued, and a new therapy can be resumed after 2–3 months. In case of good effect, the treatment should continue according to the following schedule:Fourth to 12th day: one tablet every 2 and 1/2 h (five tablets daily)Thirteenth to 16th day: one tablet every 3 h (four tablets daily) Seventeenth to 20th day: one tablet every 5 h (three tablets daily)Twenty-first to 25th day: one to two tablets daily
• Clinical Use: Cytisine has been used in the Eastern European countries for many years because of its proven benefits and low cost as compared with other cessation medications. A recent clinical trial in New Zealand found that at 1?month, continuous abstinence from smoking was reported for 40% of participants receiving cytisine (264 of 655) and 31% of participants receiving nicotine replacement therapy (203 of 655) . The available data indicates that cytisine is generally well-tolerated in human. However, high dosages of cytisine can be toxic.

Technology Process of Pharmakon1600-01504027

There total 48 articles about Pharmakon1600-01504027 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: 96.0%

N-nosyl-(?)-cytisine → cytisine (485-35-8)

Guidance literature:

With potassium carbonate; thiophenol; In N,N-dimethyl-formamide; acetonitrile; at 45 ℃; for 0.5h;

DOI:10.1021/acs.joc.8b01156

Reference yield: 79.0%

(1R,9R)-11-tert-butoxycarbonyl-7,11-diazatricyclo[7.3.1.02,7]tridec-2,4-dien-6,10-dione → cytisine (485-35-8)

Guidance literature:

(1R,9R)-11-tert-butoxycarbonyl-7,11-diazatricyclo[7.3.1.0^2,7]tridec-2,4-dien-6,10-dione; With methanol; sodium tetrahydroborate; at 0 - 20 ℃; for 2h;

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 15h;

DOI:10.1002/anie.201712852

Reference yield: 78.0%

(6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine (667940-15-0) → cytisine (485-35-8)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 3h; Heating;

DOI:10.1021/ol0361507

upstream raw materials:

1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one

(6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine

(3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester

(3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester

Downstream raw materials:

N-(2-Hydroxyethyl)cytisine

(-)-rhombifoline

(1R,5S)-3-benzyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido-[1,2-a][1,5]diazocin-8-one

(-)-N-methylcystine

Refernces

• 1、 Barát, Viktor,Csókás, Dániel,Bates, Roderick W.. "Synthesis of (-)-Cytisine Using a 6- endo aza-Michael Addition". . p. 9088 - 9095. Retrieved 2018/07/25.
• 2、 Danieli, Bruno,Lesma, Giordano,Passarella, Daniele,Sacchetti, Alessandro,Silvani, Alessandra,Virdis, Andrea. "Total Enantioselective Synthesis of (-)-Cytisine". . p. 493 - 496. Retrieved 2007/10/03.