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Substance Name: Amygdalin
RN: 29883-15-6
UNII: 214UUQ9N0H
InChIKey: XUCIJNAGGSZNQT-JHSLDZJXSA-N

Note

  • A cyanogenic glycoside found in the seeds of Rosaceae.

Molecular Formula

  • C20-H27-N-O11

Molecular Weight

  • 457.4293
 

Classification Codes

  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Amygdalin

MeSH Heading

  • Amygdalin

Synonyms

  • (R)-alpha-((6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy)benzeneacetonitrile
  • 5-17-08-00118 (Beilstein Handbook Reference)
  • Amygdalin
  • Amygdaloside
  • Benzeneacetonitrile, alpha-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-, (R)-
  • BRN 0066856
  • D(-)-Mandelonitrile-beta-D-gentiobioside
  • D-Amygdalin
  • D-Mandelonitrile-beta-D-glucosido-6-beta-D-glucoside
  • EINECS 249-925-3
  • HSDB 3559
  • Mandelonitrile-beta-gentiobioside
  • NSC 15780
  • NSC-15780
  • R-Amygdalin
  • UNII-214UUQ9N0H

Systematic Names

  • Amygdalin
  • Benzeneacetonitrile, alpha-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-, (R)- (9CI)
  • D(-)-Mandelonitrile-beta-D-gentiobioside

Registry Numbers

CAS Registry Number

  • 29883-15-6

FDA UNII

  • 214UUQ9N0H

Other Registry Number

  • 672-72-0

System Generated Number

  • 0029883156

Structure Descriptors

InChI

1S/C20H27NO11/c21-6-10(9-4-2-1-3-5-9)30-20-18(28)16(26)14(24)12(32-20)8-29-19-17(27)15(25)13(23)11(7-22)31-19/h1-5,10-20,22-28H,7-8H2/t10-,11+,12+,13+,14+,15-,16-,17+,18+,19+,20+/m0/s1

InChIKey

XUCIJNAGGSZNQT-JHSLDZJXSA-N

Smiles

OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@H](C#N)c3ccccc3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 100mg/kg (100mg/kg)   National Technical Information Service. Vol. PB288-559,
infant LDLo oral 50mg/kg (50mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
JAMA, Journal of the American Medical Association. Vol. 238, Pg. 482, 1977.
monkey LDLo oral 167mg/kg (167mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. PB288-559,
mouse LD50 oral 443mg/kg (443mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 29, Pg. 1291, 1987.
rat LD50 oral 405mg/kg (405mg/kg)   National Technical Information Service. Vol. PB288-558,

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 224.5 deg C   EXP
log P (octanol-water) -4.340 (none)   EST
Atmospheric OH Rate Constant 1.34E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.