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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) BEHAVIORAL: MUSCLE WEAKNESS

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
JAMA, Journal of the American Medical Association. Vol. 238, Pg. 1361, 1977.
rabbit LD50 intravenous 687uL/kg (0.687mL/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: ATAXIA
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"

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
JAMA, Journal of the American Medical Association. Vol. 239, Pg. 1532, 1978.
women TDLo multiple routes 4170mg/kg/8W (4170mg/kg)   Cancer Treatment Reports. Vol. 62, Pg. 169, 1978.
women TDLo multiple routes 4170mg/kg/8W (4170mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Cancer Treatment Reports. Vol. 62, Pg. 169, 1978.
women TDLo oral 60mg/kg (60mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

LIVER: FATTY LIVER DEGERATION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Southern Medical Journal. Vol. 79, Pg. 259, 1986.