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(1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1-,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenemethanamine hydrochloride

Basic information Safety Supplier Related

(1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1-,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenemethanamine hydrochloride Basic information

Product Name:
(1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1-,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenemethanamine hydrochloride
Synonyms:
  • (1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1-,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenemethanamine hydrochloride
  • (+)-DehydroabiethylaMine Hydrochloride
  • 13-Isopropyl-podocarpa-8,11,13-trien-15-aMine Hydrochloride
  • ((1S,4aS)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methanamine hydrochloride
  • Dehydroabietylamine Hydrochloride
  • DehydroabiethylaMine Hydrochloride
  • [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine
CAS:
16496-99-4
MF:
C20H32ClN
MW:
321.93
Product Categories:
  • Antifungal
  • Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
Mol File:
16496-99-4.mol
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(1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1-,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenemethanamine hydrochloride Chemical Properties

storage temp. 
-20°
solubility 
Soluble in DMSO (up to 40 mg/ml) or in Water (up to 9 mg/ml).
form 
solid
color 
Off-white or beige
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month.
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(1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1-,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenemethanamine hydrochloride Usage And Synthesis

Description

Leelamine HCl (16496-99-4) is a lysosomotropic, intracellular cholesterol transport inhibitor with potential chemotherapeutic activity. Induces cholesterol accumulation in lysosomal/endosomal cell compartments via inhibition of autophagic flux.1?Induces apoptosis in breast cancer2, melanoma3?and prostate cancer cells4. A selective inducer of cytochrome P450 2B.5?Inhibits pyruvate dehydrogenase kinase (PDK), IC50=9.5 μM.6

Uses

Dehydroabiethylamine is a primary amine with high molecular weight; shows a strong antibiotic effect with a broad spectrum of activity against Staphylococcus p.a. (sic), Escherichia coli, Mycobacterium tuberculosis, and Candida albicans.

Uses

Resolving agent for carboxylic acids

IC 50

CB1

References

[1] OMER F KUZU. Leelamine mediates cancer cell death through inhibition of intracellular cholesterol transport.[J]. Molecular Cancer Therapeutics, 2014, 13 7: 1690-1703. DOI:10.1158/1535-7163.mct-13-0868
[2] ANURADHA SEHRAWAT. Cancer-selective death of human breast cancer cells by leelamine is mediated by bax and bak activation.[J]. Molecular Carcinogenesis, 2017, 56 2: 337-348. DOI:10.1002/mc.22497
[3] YU-CHI CHEN. Targeting cholesterol transport in circulating melanoma cells to inhibit metastasis[J]. Pigment Cell & Melanoma Research, 2017, 30 6: 541-552. DOI:10.1111/pcmr.12614
[4] KRISHNA B SINGH  Shivendra V S  Xinhua Ji. Therapeutic Potential of Leelamine, a Novel Inhibitor of Androgen Receptor and Castration-Resistant Prostate Cancer.[J]. Molecular Cancer Therapeutics, 2018, 17 10: 2079-2090. DOI:10.1158/1535-7163.mct-18-0117
[5] JUHEE SIM. Selective induction of hepatic cytochrome P450 2B activity by leelamine in vivo, as a potent novel inducer[J]. Archives of Pharmacal Research, 2014, 38 5: 725-733. DOI:10.1007/s12272-014-0443-0
[6] THOMAS D. AICHER ∗. Triterpene and diterpene inhibitors of pyruvate dehydrogenase kinase (PDK)[J]. Bioorganic & Medicinal Chemistry Letters, 1999, 9 15: Pages 2223-2228. DOI:10.1016/s0960-894x(99)00380-7

(1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1-,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenemethanamine hydrochlorideSupplier

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(1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1-,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenemethanamine hydrochloride(16496-99-4)Related Product Information