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CAS

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1019-45-0

N,N-Dimethyl-5-methoxytryptamine, also known as 5-Methoxy-N,N-dimethyltryptamine, is a tryptamine alkaloid that is N,N-dimethyltryptamine substituted by a methoxy group at position 5. It is obtained from Desmodium pulchellum Benth ex Baker and Phalaris tuberosa L. This indole alkaloid is best crystallized from Et20-light petroleum, yielding colorless rectangular plates. It is optically inactive, and the ultraviolet spectrum has absorption maxima at 224, 277, and 296 mil. It forms a crystalline picrate as orange-yellow needles, m.p. 176-7°C, and the methiodide, m.p. 181-2°C. As a chemical, it is an off-white to slightly yellow crystalline powder.

1019-45-0 Suppliers

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  • 1019-45-0 Structure

  • Basic information

    1. Product Name: N,N-Dimethyl-5-methoxytryptamine
    2. Synonyms: 3-(2-DIMETHYLAMINOETHYL)-5-METHOXYINDOLE;5-MEO-DMT;5-OME-DMT;5-METHOXY-DMT;5-METHOXY-N,N-DIMETHYLTRYPTAMINE;TIMTEC-BB SBB003367;N-[2-(5-METHOXY-1H-INDOL-3-YL)ETHYL]-N,N-DIMETHYLAMINE;N,N-DIMETHYL-5-METHOXYTRYPTAMINE
    3. CAS NO:1019-45-0
    4. Molecular Formula: C13H18N2O
    5. Molecular Weight: 218.29
    6. EINECS: 213-813-2
    7. Product Categories: Tryptamines;Research Chemical
    8. Mol File: 1019-45-0.mol

  • Chemical Properties

    1. Melting Point: 69 °C
    2. Boiling Point: 358.99°C (rough estimate)
    3. Flash Point: 177.9 °C
    4. Appearance: off-white to slightly yellow crystalline powder
    5. Density: 1.0346 (rough estimate)
    6. Vapor Pressure: 1.1E-05mmHg at 25°C
    7. Refractive Index: 1.6450 (estimate)
    8. Storage Temp.: 0-6°C
    9. Solubility: Chloroform (Slightly), Methanol (Slightly)
    10. PKA: 16.94±0.30(Predicted)
    11. Water Solubility: PRACTICALLY INSOLUBLE
    12. CAS DataBase Reference: N,N-Dimethyl-5-methoxytryptamine(CAS DataBase Reference)
    13. NIST Chemistry Reference: N,N-Dimethyl-5-methoxytryptamine(1019-45-0)
    14. EPA Substance Registry System: N,N-Dimethyl-5-methoxytryptamine(1019-45-0)

  • Safety Data

    1. Hazard Codes: C,Xn
    2. Statements: 20-34-43-21/22
    3. Safety Statements: 22-26-28A-36/37/39-45-36-24/25
    4. RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
    5. WGK Germany:
    6. RTECS: NL7380000
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 1019-45-0(Hazardous Substances Data)

1019-45-0 Usage

Uses

Used in Pharmaceutical Industry:
N,N-Dimethyl-5-methoxytryptamine is used as a hallucinogen and non-selective serotonin receptor agonist for the study of mammalian hormones to stimulate cAMP formation by colliculi neurons and mediate serotoninergic receptors.
Used in Ethnobotanical Industry:
It is a natural hallucinogen component of Ayahuasca, an Amazonian beverage, and is currently being made as a designer drug.

References

Culvenor, Brown, Smith., Austral. J. Chern., 17, 1301 (1964) Ghosal, Mukherjee., Chern. Ind., 793 (1965) Ghosal, Mukherjee., J. Org. Chern., 31, 2284 (1966)

Check Digit Verification of cas no

The CAS Registry Mumber 1019-45-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,1 and 9 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1019-45:
(6*1)+(5*0)+(4*1)+(3*9)+(2*4)+(1*5)=50
50 % 10 = 0
So 1019-45-0 is a valid CAS Registry Number.
InChI:InChI=1/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3/p+1

1019-45-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-methoxy-N,N-dimethyltryptamine

1.2 Other means of identification

Product number -
Other names 2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1019-45-0 SDS

1019-45-0Relevant articles and documents

Design, synthesis and biological evaluation of novel chiral oxazino-indoles as potential and selective neuroprotective agents against Aβ25–35-induced neuronal damage

Chen, Jing,Tao, Ling-Xue,Xiao, Wei,Ji, Sha-Sha,Wang, Jian-Rong,Li, Xu-Wen,Zhang, Hai-Yan,Guo, Yue-Wei

, p. 3765 - 3769 (2016)

A series of chiral oxazino-indoles have been synthesized via a key intermolecular oxa-Pictet–Spengler reaction. These compounds exhibited significant and selective neuroprotective effects against Aβ25–35-induced neuronal damage. This is the first report of evaluating the influence of chiral diversity of oxazino-indoles on their neuroprotective activities, with the structure–activity relationship been analyzed. The highly active compounds 3f, 3g, 4g, 4h, and 6b all performed over 90% cell protection, providing a new direction for the development of neuroprotective agents against Alzheimer's disease.

Synthesis of 131I derivatives of indolealkylamines for brain mapping

Sintas, Jose A.,Vitale, Arturo A.

, p. 677 - 684 (1997)

The synthesis and spectral properties of new radioiodinated indolealkylamines like 2-[131 I]-iodo-N,N-dimethyltryptamine, 2-[131 I]-iodo-N-methyltryptamine, 2-[131 I]-iodo-5-methoxy-N,N-dimethyltryptamine, 2-[131 I]-iodo-5-hydroxy-N,N-dimethyltryptamine (2-[131 I]-iodo-bufotenine), and 2-[131I]-iodo-tryptamine and the known 2-[131I]-iodo-N-acetyl-5-methoxy-tryptamine (2-[131I]-iodo-melatonine) are described herein. These were synthesized by a high-yield novel method, and their spectral properties are fully described. These compounds are of biological importance and can be used for brain mapping with SPECT technology.

Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols

Biswas, Nandita,Sharma, Rahul,Srimani, Dipankar

supporting information, p. 2902 - 2910 (2020/06/03)

Herein, we presented Ru-SNS complex that serves as a useful catalyst for C-3 alkylation of 1H-indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C-3 alkylated indoles directly from 2-(2-nitrophenyl)ethan-1-ol and alcohols catalysed by a Ru-complex via “borrowing hydrogen” strategy is reported. This protocol provides an atom-economical sustainable route to access structurally important compounds like arundine, vibrindole A and tryptamine based derivatives. (Figure presented.).

N-SUBSTITUTED INDOLES AND OTHER HETEROCYCLES FOR TREATING BRAIN DISORDERS

-

Paragraph 0218, (2020/09/12)

The present invention provides N-substituted indoles and other heterocycles and methods of using the compounds for treating brain disorders.

Identification of Psychoplastogenic N, N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies

Dunlap, Lee E.,Azinfar, Arya,Ly, Calvin,Cameron, Lindsay P.,Viswanathan, Jayashri,Tombari, Robert J.,Myers-Turnbull, Douglas,Taylor, Jack C.,Grodzki, Ana Cristina,Lein, Pamela J.,Kokel, David,Olson, David E.

, p. 1142 - 1155 (2020/03/10)

Ketamine, N,N-dimethyltryptamine (DMT), and other psychoplastogens possess enormous potential as neurotherapeutics due to their ability to potently promote neuronal growth. Here, we report the first-ever structure-Activity relationship study with the explicit goal of identifying novel psychoplastogens. We have discovered several key features of the psychoplastogenic pharmacophore and used this information to develop N,N-dimethylaminoisotryptamine (isoDMT) psychoplastogens that are easier to synthesize, have improved physicochemical properties, and possess reduced hallucinogenic potential as compared to their DMT counterparts.

Indole derivatives and its application on the medicament

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Paragraph 0222; 0224-0227; 0252; 0254-0257, (2019/03/28)

The invention provides indole derivatives or stereisomers, tautomers, nitrogen oxides, solvate, metabolic products, pharmaceutically acceptable salts or prodrugs thereof for treating the alzheimer disease. The invention further discloses a pharmaceutical composition containing the compounds and a method of using the compounds or the pharmaceutical composition thereof to treat the alzheimer disease.

NOVEL COMPOSITIONS AND METHODS FOR TREATING CANCER

-

Paragraph 0489-0490, (2013/05/21)

Provided herein are methods and compositions inter alia for treating diseases, including hyperproliferative diseases, migraine headaches, and depression.

Synthesis and structureactivity relationship of novel conformationally restricted analogues of serotonin as 5-HT6 receptor ligands

Nirogi, Ramakrishna V.S.,Kambhampati, Ramasastri,Kothmirkar, Prabhakar,Konda, Jagadishbabu,Bandyala, Thrinath Reddy,Gudla, Parandhama,Arepalli, Sobhanadri,Gangadasari, Narasimhareddy P.,Shinde, Anil K.,Deshpande, Amol D.,Dwarampudi, Adireddy,Chindhe, Anil K.,Dubey, Pramod Kumar

scheme or table, p. 443 - 450 (2012/08/28)

5-Hydroxytryptamine 6 receptors (5-HT6R) are being perceived as the possible target for treatment of cognitive disorders as well as obesity. The present article deals with the design, synthesis, in vitro binding and structureactivity relationship of a novel series of tetracyclic tryptamines with the rigidized N-arylsulphonyl, N-arylcarbonyl and N-benzyl substituents as 5-HT6 receptor ligands. The chiral sulphonyl derivatives 15a and 17a showed high affinity at 5-HT6R with the Ki of 23.4 and 20.5nM, respectively. The lead compound from the series 15a has acceptable ADME properties, adequate brain penetration and is active in animal models of cognition like Novel Object Recognition Task (NORT) and water maze.

Novel 5-HT7 receptor inverse agonists. Synthesis and molecular modeling of arylpiperazine- and 1,2,3,4-tetrahydroisoquinoline-based arylsulfonamides.

Vermeulen, Erik S,van Smeden, Marjan,Schmidt, Anne W,Sprouse, Jeffrey S,Wikstroem, Hakan V,Grol, Cor J

, p. 5451 - 5466 (2007/10/03)

A series of arylpiperazine- and 1,2,3,4-tetrahydroisoquinoline-based arylsulfonamides was synthesized and evaluated for their interactions with the constitutively active 5-HT7 receptor. Effects on basal adenylate cyclase activity were measured using HEK-293 cells expressing the rat 5-HT7. All ligands produced a decrease of adenylate cyclase activity, indicative of their inverse agonism. Additionally, computational studies with a set of 22 inverse agonists, including these novel inverse agonists and inverse agonists known from literature, resulted in a pharmacophore model and a CoMFA model (R2 = 0.97, SE = 0.18). Docking of inverse agonists at the binding site of a model of the helical parts of the 5-HT7 receptor, based on the alpha carbon template for 7-TM GPCRs, revealed interesting molecular interactions and a possible explanation for observed structure-activity relationships.

MELATONIN DERIVATIVES AND THEIR USE FOR TREATING NEUROLOGICAL DYSFUNCTIONS

-

Page 37, (2008/06/13)

The present invention relates to compounds of the general formula (1): wherein R1, R2, R3, R4 and R5 are H or a moiety of the formula : -(R6)n-R7; with R6 is a is an alkyl chain and R7 is, a moiety selected in the group consisting of -Cn,H2n2,+I, a cycloalkyl moiety, -N(Cn,H2n,+I)(Cn,H2n,+1), -NH-cycloalkyl, -O(Cn,H2n'+I), -0-cycloalkyl, =O, =S, -NO2, -I, -Br, -Cl, -F, -CF3, -OCF3, -COOH, -S03H, -P03H2, -CN, A3 and A4 are, C, N,O or S;m is from 0 to 2; and to their use for the treatment and/or prevention of diseases and conditions mediated by the imbalance of acetylcholine, and for treating and/or preventing glutamate excitotoxicity.