Alpha-ethyltryptamine

Các tên gọi khác (3) :

Etryptamine
α-ethyltryptamine
αET

stimulants

Thuốc Gốc

Small Molecule

CAS: 2235-90-7

CTHH: C₁₂H₁₆N₂

PTK: 188.2688

In the 1960's, alpha-ethyltryptamine (αET), a non hydrazine reversible monoamine oxidase inhibitor, was developed in the United States by the Upjohn chemical company for use as an antidepressant. αET was an FDA approved antidepressant under the name Monase. However, in 1962, after the discovery of an unacceptable incidence of agranulocytosis, the development of Monase was halted and the drug was withdrawn from potential market use. In 1993, the US Drug Enforcement Administration added αET to Schedule I of its Schedules of Controlled Substances, after an increasing incidence of its use as a recreational drug in the 1980's. Currently, αET is an illegal substance; however, it's activity is still under scientific investigation. αET is a stimulant and hallucinogen, but it is less stimulating and hallucinogenic than alpha-methyltryptamine, a closely related compound. Instead, the effects of αET, a tryptamine derivative, more closely resemble the amphetamine derived drug 3,4-methylenedioxy-N-methylamphetamine (MDMA). Similarly to MDMA, αET has been shown to release serotonin pre-synaptically, as well as lesser amounts of norepinephrine and dopamine. Like MDMA, increases in locomotor activity and mood elevation can be seen post administration.

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₁₂H₁₆N₂

Phân tử khối

188.2688

Monoisotopic mass

188.131348522

InChI

InChI=1S/C12H16N2/c1-2-10(13)7-9-8-14-12-6-4-3-5-11(9)12/h3-6,8,10,14H,2,7,13H2,1H3

InChI Key

InChIKey=ZXUMUPVQYAFTLF-UHFFFAOYSA-N

IUPAC Name

1-(1H-indol-3-yl)butan-2-amine

Traditional IUPAC Name

1-(1H-indol-3-yl)butan-2-amine

SMILES

CCC(N)CC1=CNC2=CC=CC=C12

Độ tan chảy

221

Độ hòa tan

510 mg/L

logP

2.43

logS

-2.57

pKa (strongest acidic)

17.13

pKa (Strongest Basic)

9.99

PSA

41.81 Å²

Refractivity

59.32 m³·mol^-1

Polarizability

22.14 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

Rule of Five

true

Ghose Filter

true

Dược Lực Học : αET is a stimulant and psychedelic with MDMA like physiological effects. Like MDMA, increases in locomotor activity and mood elevation can be seen post administration. [2]

Cơ Chế Tác Dụng : In the 1960's, alpha-ethyltryptamine (αET), a non hydrazine reversible monoamine oxidase inhibitor, was developed in the United States by the Upjohn chemical company for use as an antidepressant. αET was an FDA approved antidepressant under the name Monase. However, in 1962, after the discovery of an unacceptable incidence of agranulocytosis, the development of Monase was halted and the drug was withdrawn from potential market use. In 1993, the US Drug Enforcement Administration added αET to Schedule I of its Schedules of Controlled Substances, after an increasing incidence of its use as a recreational drug in the 1980's. Currently, αET is an illegal substance; however, it's activity is still under scientific investigation. αET is a stimulant and hallucinogen, but it is less stimulating and hallucinogenic than alpha-methyltryptamine, a closely related compound. Instead, the effects of αET, a tryptamine derivative, more closely resemble the amphetamine derived drug 3,4-methylenedioxy-N-methylamphetamine (MDMA). Similarly to MDMA, αET has been shown to release serotonin pre-synaptically, as well as lesser amounts of norepinephrine and dopamine. Like MDMA, increases in locomotor activity and mood elevation can be seen post administration. The mechanism of action responsible for its antidepressant activity was believed to lie in its ability to inhibit monoamine oxidase, while its stimulant activity on the central nervous system appeared to result from its structural similarity to indole-based psychedelics. [5] Research discovered αET to be both a monoamine oxidase inhibitor and a potent monoamine releasing agent capable of serotonergic neurotoxicity. [3] The ability to release serotonin was linked to αET's MDMA like properties. [2] αET has been shown to release serotonin pre-synaptically, as well as lesser amounts of norepinephrine and dopamine.

Chỉ Định : Developed in the 1960's for use as an antidepressant before market withdrawal in 1962.

Dữ Kiện Thương Mại

Nhà Sản Xuất

Công ty : Upjohn

Sản phẩm biệt dược : Monase

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB01546

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=8367

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507084

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C06213

KEGG Drug

http://www.genome.jp/dbget-bin/www_bget?drug:D04092

ChemSpider

http://www.chemspider.com/Chemical-Structure.8064.html

Wikipedia

http://en.wikipedia.org/wiki/Alpha-ethyltryptamine

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