304-21-2 Usage
Uses
Used in Pharmaceutical Industry:
Harmaline is used as a CNS stimulant, which may act through NMDA receptors. It is known for its potential antiparkinsonian effects, making it a promising candidate for the treatment of Parkinson's disease.
Used in Neurological Applications:
As a reversible inhibitor of MAO-A, HARMALINE is used in the treatment of various neurological disorders. Its ability to inhibit monoamine oxidase-A, an enzyme involved in the breakdown of neurotransmitters, can help regulate mood and cognitive function.
Used in Research and Development:
Harmaline's unique chemical structure and pharmacological properties make it an interesting compound for research and development in the fields of neuroscience and drug discovery. It can be used as a starting point for the development of new drugs targeting the central nervous system and other related conditions.
Synthesis Reference(s)
Canadian Journal of Chemistry, 37, p. 1851, 1959 DOI: 10.1139/v59-272
Purification Methods
Recrystallise harmaline from MeOH and sublime it at high vacuum. It has UV in MeOH a
Check Digit Verification of cas no
The CAS Registry Mumber 304-21-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,0 and 4 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 304-21:
(5*3)+(4*0)+(3*4)+(2*2)+(1*1)=32
32 % 10 = 2
So 304-21-2 is a valid CAS Registry Number.
InChI:InChI=1/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,15H,5-6H2,1-2H3
304-21-2Relevant articles and documents
Harmaline Analogs as Substrate-Selective Cyclooxygenase-2 Inhibitors
Uddin, Md. Jashim,Xu, Shu,Crews, Brenda C.,Aleem, Ansari M.,Ghebreselasie, Kebreab,Banerjee, Surajit,Marnett, Lawrence J.
, p. 1881 - 1885 (2020)
We report the design, synthesis, and evaluation of a series of harmaline analogs as selective inhibitors of 2-arachidonylglycerol (2-AG) oxygenation over arachidonic acid (AA) oxygenation by purified cyclooxygenase-2 (COX-2). A fused tricyclic harmaline analog containing a CH3O substituent at C-6 and a CH3 group at the C-1 position of 4,9-dihydro-3H-pyrido[3,4-b]indole (compound 3) was the best substrate-selective COX-2 inhibitor of those evaluated, exhibiting a 2AG-selective COX-2 inhibitory IC50 of 0.022 μM as compared to >1 μM for AA. The 2.66 ? resolution crystal complex of COX-2 with compound 3 revealed that this series of tricyclic indoles binds in the cyclooxygenase channel by flipping the side chain of L531 toward the dimer interface. This novel tricyclic indole series provides the foundation for the development of promising substrate-selective molecules capable of increasing endocannabinoid (EC) levels in the brain to offer new treatments for a variety of diseases, from pain and inflammation to stress and anxiety disorders.
