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Substance Name: Laetrile
RN: 1332-94-1
InChIKey: XLSLFPQAPYONPW-WHUHBCJBSA-N

Note

  • A cyanogenic glycoside found in the seeds of Rosaceae.

    NCI: Originally, the name laetrile was the contraction of laevo-mandelonitrile glucoside, a cyanogenic glycoside found naturally in some plants. Over the years the meaning of laetrile has changed. There are now preparations called Laetrile where amygdalin is the major constituent. Laetrile and amygdalin are often used interchangeably, but are different agents. Cyanide and benzaldehyde are metabolites of both laetrile and amygdalin. Both metabolites may possess antineoplastic properties. Laetrile has been used as an anticancer treatment in humans worldwide, but scientific evidence does not support its effectiveness. It is not approved for use in the United States. (NCI Drug Dictionary)

Molecular Formula

  • C14-H15-N-O7

Molecular Weight

  • 309.272
 

Classification Codes

  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
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Names and Synonyms

Synonyms

  • beta-D-Glucopyranosiduronic acid, alpha-cyanobenzyl
  • BRN 5608756
  • Cyanophenylmethyl-beta-D-glucopyranosiduronic acid
  • l-Mandelonitrile-beta-glucuronoside
  • Laetrile
  • Mandelonitrile beta-glucuronide
  • NSC 103055
  • Vitamin B(sub 17)
  • Vitamin B17

Systematic Names

  • beta-D-Glucopyranosiduronic acid, cyanophenylmethyl, (R)- (9CI)
  • Laetrile

Registry Numbers

CAS Registry Number

  • 1332-94-1

Other Registry Number

  • 57534-26-6

System Generated Number

  • 0001332941

Structure Descriptors

InChI

1S/C14H15NO7/c15-6-8(7-4-2-1-3-5-7)21-14-11(18)9(16)10(17)12(22-14)13(19)20/h1-5,8-12,14,16-18H,(H,19,20)/t8-,9-,10-,11+,12-,14+/m0/s1

InChIKey

XLSLFPQAPYONPW-WHUHBCJBSA-N

Smiles

O1[C@@H](O[C@@H](C#N)c2ccccc2)[C@@H]([C@H]([C@@H]([C@H]1C(=O)O)O)O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 1286mg/kg/24W (1286mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: MUSCLE WEAKNESS
JAMA, Journal of the American Medical Association. Vol. 238, Pg. 1361, 1977.
rabbit LD50 intravenous 687uL/kg (0.687mL/kg) BEHAVIORAL: ATAXIA

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE
United States Patent Document. Vol. #4337760,
rat LDLo intraperitoneal 250mg/kg (250mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
JAMA, Journal of the American Medical Association. Vol. 242, Pg. 169, 1979.
women LDLo oral 198mg/kg (198mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
JAMA, Journal of the American Medical Association. Vol. 239, Pg. 1532, 1978.
women TDLo multiple routes 4170mg/kg/8W (4170mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

GASTROINTESTINAL: NAUSEA OR VOMITING
Cancer Treatment Reports. Vol. 62, Pg. 169, 1978.
women TDLo oral 60mg/kg (60mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LIVER: FATTY LIVER DEGERATION
Southern Medical Journal. Vol. 79, Pg. 259, 1986.