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Ornithine is methylated to N-methylornithine and when decarboxylated, becomes N-methylputrescine. 4-methylaminobutanal is yielded from the oxidation of the primary amino-group. 4-methylaminobutanal then cyclizes to an N-methyl-l-pyrrolinium salt. The condensation of the pyrrolinium salt with
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503:"USDA, ARS, National Genetic Resources Program. Phytochemical and Ethnobotanical Databases. National Germplasm Resources Laboratory, Beltsville, Maryland"
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acetoacetyl coenzyme A yields hygrine. Finally, the condensation of the hygrine molecule with another molecule of pyrrolidinium salt yields cuscohygrine.
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Cuscohygrine is an oil that can be distilled without decomposition only in vacuum. It is soluble in water. It also forms a crystalline tri
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O'Donovan, D. G.; Keogh, M. F. (1969). "The role of hygrine in the biosynthesis of cuscohygrine and hyoscyamine".
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InChI=1S/C13H24N2O/c1-14-7-3-5-11(14)9-13(16)10-12-6-4-8-15(12)2/h11-12H,3-10H2,1-2H3/t11-,12+
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in 1889 as an alkaloid accompanying cocaine in coca leaves (also known as Cusco-leaves).
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species. Cuscohygrine usually occurs along with other, more potent alkaloids such as
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The
Vegetable Alkaloids. With particular reference to their chemical constitution
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Except where otherwise noted, data are given for materials in their
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40–41 °C (104–106 °F; 313–314 K) (trihydrate)
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384:. It can also be extracted from plants of the family
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482:Journal of the Chemical Society C: Organic
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411:Cuscohygrine, along with the related
260:Key: ZEBIACKKLGVLFZ-TXEJJXNPSA-N
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546:Alkaloids found in Erythroxylum coca
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394:(deadly nightshade) and various
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355:(at 25 °C , 100 kPa).
429:which melts at 40–41 °C.
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551:Alkaloids found in Solanaceae
526:. London: Chapman & Hall.
445:Biosynthesis of Cuscohygrine
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418:, was first isolated by
522:Dr. Ame Pictet (1904).
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541:Pyrrolidine alkaloids
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281:CN1CCC1CC(=O)C2CCCN2C
509:on December 12, 2012
490:10.1039/J39690000223
46:Preferred IUPAC name
461:Dihydrocuscohygrine
335: g·mol
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373:is a bis N-methyl
359:Infobox references
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391:Atropa belladonna
367:Chemical compound
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213:CompTox Dashboard
98:Interactive image
50:1--3-propan-2-one
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505:. Archived from
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297:Chemical formula
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484:(2): 223–226.
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17:Cuscohygrine
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511:. Retrieved
507:the original
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433:Biosynthesis
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388:, including
371:Cuscohygrine
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57:Identifiers
382:coca plants
375:pyrrolidine
290:Properties
535:Categories
467:References
413:metabolite
386:Solanaceae
328:Molar mass
201:93FJ3823VL
127:ChemSpider
85:3D model (
64:CAS Number
380:found in
513:July 14,
450:See also
402:atropine
378:alkaloid
136:21864896
74:454-14-8
556:Ketones
427:hydrate
416:hygrine
406:cocaine
333:224.348
181:1201543
168:PubChem
397:Datura
274:SMILES
156:C06521
116:B05209
108:3DMet
40:Names
249:InChI
87:JSmol
515:2005
192:UNII
147:KEGG
486:doi
404:or
218:EPA
171:CID
537::
408:.
312:24
306:13
517:.
492:.
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321:O
318:2
315:N
309:H
303:C
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216:(
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Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
