304-54-1

Basic information

• Product Name: (+/-)-alpha-methyltryptamine
• Synonyms: ALPHA-METHYLTRYPTAMINE;(+-)-alpha-Methyl-1H-indole-3-ethanamine;1H-Indole-3-ethanamine, alpha-methyl-, (+-)- (9ci)
• CAS NO: 304-54-1
• Molecular Formula: C11H14N2
• Molecular Weight: 174.24
• Mol File: 304-54-1.mol
• Article Data: 32

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+/-)-alpha-methyltryptamine(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-alpha-methyltryptamine(304-54-1)
• EPA Substance Registry System: (+/-)-alpha-methyltryptamine(304-54-1)

Safety Data

• Hazardous Substances Data: 304-54-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 4294, 1986 DOI: 10.1021/jo00372a037

Upstream product

• 64252-02-4 3-(β-nitro-β-methylvinyl)indole 
• 4771-72-6 α-methyl-β-(3-indolyl)-1-nitroethane 
• 487-89-8 Indole-3-carboxaldehyde 
• 22693-51-2 3-(2-nitroprop-1-en-1-yl)-1H-indole 
• 120-72-9 indole 
• 1201-26-9 3-(1H-indolyl)acetone 
• 299-26-3 1-(1H-indol-3-yl)propan-2-amine 
• 371-27-7 2,2,2-trifluoroethylbutyrate 
• 113997-60-7 (S)-1-(1H-indol-3-yl)-N-((R)-1-phenylethyl)propan-2-amine 
• 113997-59-4 (S,S)-N-α-phenetyl-1-indol-3-yl-2-aminopropane 
• 108-20-3 di-isopropyl ether 
• 61535-48-6 C₂₆H₂₆N₂O₅S 
• 3938-96-3 ethyl 2-methoxyacetate 
• 113997-58-3 (R)-1-(1H-indol-3-yl)-N-((R)-1-phenylethyl)propan-2-amine 

Downstream Products

• 86995-94-0 1-Indolyl-3-isopropylmethylpropargylamine 
• 1193314-21-4 (1R,3S)-5'-chloro-3-methyl-2,3,4,9-tetrahydrospiro[β-carboline-1,3'-indol]-2'(1'H)-one 
• 1292798-84-5 (R)-N-[1-(1H-indol-3-yl)propan-2-yl]-2-methoxyacetamide 
• 7795-51-9 (+)-alpha-Methyltryptamine 
• 1612181-94-8 6-(3-chloro-2-methylphenyl)-4-N-[1-(1H-indol-3-yl)propan-2-yl]pyrimidine-2,4-diamine 
• 1639042-08-2 (E)-3-(3,5-difluoro-4-((1R,3R)-2-(2-fluoro-2-methyl-propyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenyl)acrylic acid 

Relevant articles and documents

Stereoselective Cascade to C3-Methylated Strictosidine Derivatives Employing Transaminases and Strictosidine Synthases

(S)-Strictosidine represents the first key intermediate in the biosynthesis of several pharmaceutically relevant monoterpenoid indole alkaloids. Optically pure C3-methyl-substituted strictosidine derivatives were prepared by setting up the two stereogenic centers at the β-carboline core via two enzymatic steps catalyzed by the enzymes transaminase and strictosidine synthase in a one-pot cascade fashion. The two enzymatic steps were performed simultaneously as well as in a stepwise fashion. The amination of the prochiral ketones led to optically pure amines with up to >98% enantiomeric excess. Depending on the enzyme used, the (S)- and (R)-enantiomers were prepared in most cases. Selected amines were then condensed with secologanin in a Pictet-Spengler reaction catalyzed by strictosidine synthase leading to diastereomerically pure products (>98% diastereomeric excess).

Efficient Manufacturing Process for the Selective Estrogen Receptor Degrader GDC-9545 (Giredestrant) via a Crystallization-Driven Diastereoselective Pictet-Spengler Condensation

GDC-9545 is a selective estrogen receptor degrader that is being developed as a treatment for ER+/HER2- breast cancer. A robust, convergent manufacturing process for GDC-9545 was developed. The process features a Wenker aziridine synthesis to produce the key starting material tryptamine 11, a highly efficient C-N coupling between aminoazetidine 9 and 2,6-difluoro-4-bromobenzaldehyde diethyl acetal (33) to construct key intermediate 10, and a crystallization-driven diastereoselective Pictet-Spengler reaction to furnish the active pharmaceutical ingredient GDC-9545·tartrate.

REGIMENS OF ESTROGEN RECEPTOR ANTAGONISTS

Provided herein are methods of administering estrogen receptor antagonists for use in treatment of cancer. The antagonists (such as a hexahydro pyrido[3,4-b]indole, AZD9496, RAD-1901, ARN-810, endoxifen, or fulvestrant) may be an inhibitor of both activating function 1 and activating function 2 of the estrogen receptor. Also provided are combinations of above inhibitors with a secondary agent, which is a CDK 4/6 inhibitor (such as, palbocociclib, ribociclib, abemaciclib, lerociclib, and trilaciclib).