J Neural Transm (Vienna)
September 12, 2009
Nicholas V. Cozzi, Anupama Gopalakrishnan, Lyndsey L. Anderson et al.
144 citations
N,N-dimethyltryptamine (DMT) is a potent plant hallucinogen that has also been found in human tissues. When ingested, DMT and related N,N-dialkyltryptamines produce an intense hallucinogenic state. Behavioral effects are mediated through various neurochemical mechanisms including activity at sigma-1 and serotonin receptors, modification of monoamine uptake and release, and competition for...
Journal of Psychoactive Drugs
June 1, 2008
Jan G. Bruhn, Hesham R. Ei-Seedi, Nikolai Stephanson et al.
11 citations
Human interest in psychoactive phenethylamines is known from the use of mescaline-containing cacti and designer drugs such as Ecstasy. From the alkaloid composition of cacti we hypothesized that substances resembling Ecstasy might occur naturally. In this article we show that lophophine, homopiperonylamine and lobivine are new minor constituents of two cactus species, Lophophora williamsii...
Journal of Medicinal Chemistry
February 24, 1998
Matthew Parker, Danuta Marona‐lewicka, Deborah M. Kurrasch et al.
25 citations
The three isomeric ring-methylated derivatives of the well-known hallucinogen and entactogen MDA (1a) were synthesized and evaluated for pharmacological activity as monoamine-releasing agents and as serotonin agonists. The 2-methyl derivative 2a and the 5-methyl derivative 2b were found to be more potent and more selective than the parent compound in inhibiting [3H]-serotonin accumulation in...
Pharmacology, biochemistry, and behavior
1990
M P Johnson, C A Mathis, Alexander T. Shulgin et al.
56 citations
Recent studies of 5-HT2 receptor binding have involved the use of radiolabeled agonists. This report describes the use of [125I]-2-(2,5-dimethoxy-4-iodophenyl)aminoethane ([125I]-2C-I) as a label for low-density 5-HT2 agonist binding sites. A nonhydrolyzable analog of GTP, GppNHp, was found to inhibit the high affinity binding of [125I]-2C-I. 5-HT and several 5-HT2 agonists and antagonists...
Ecstasy: The Clinical, Pharmacological and Neurotoxicological Effects of the Drug MDMA
1990
Alexander T. Shulgin
35 citations
There can never be a complete history of any intensely controversial topic whose proponents and skeptics state their beliefs with equal confidence. Some historical facts will rest uncontested. Many facts will be clothed in opinions that will color the way the facts are to be interpreted. Other facts will never be publicly known, for reasons of legality or privacy. And some facts may simply be...
Journal of Psychoactive Drugs
October 1, 1986
Alexander T. Shulgin
234 citations
(1986). The Background and Chemistry of MDMA. Journal of Psychoactive Drugs: Vol. 18, MDMA: Proceedings of the Conference, pp. 291-304.
Journal of Medicinal Chemistry
October 1, 1986
David E. Nichols, Andrew J. Hoffman, Robert Oberlender et al.
189 citations
The alpha-ethyl phenethylamine derivative 1-(1,3-benzodioxol-5-yl)-2-butanamine was prepared. An asymmetric synthesis was used to prepare the enantiomers of this compound and the related alpha-methyl homologue (MDA). The racemates and enantiomers of both compounds were evaluated in the two-lever drug discrimination assay in rats trained to discriminate saline from 0.08 mg/kg of LSD tartrate....
The Journal of pharmacy and pharmacology
August 1985
D Lemaire, Peyton Jacob, Alexander T. Shulgin
Four members of a new class of psychotomimetic agents have been synthesized and evaluated in man. These compounds, which incorporate a beta-methoxy group onto a beta-phenethylamine sidechain, are the first reported psychotomimetics which are structural analogues of the neurotransmitter noradrenaline. These substances are more potent than the corresponding phenethylamines (lacking a beta-methoxy...
Chemischer Informationsdienst
November 27, 1984
P. Iii Jacob, Alexander T. Shulgin
AbstractDargestellt und auf ZNS‐Wirkung untersucht werden die Verbindungen (V), (VII) und (VIII).
Journal of Medicinal Chemistry
July 1, 1984
Peyton Jacob, Alexander T. Shulgin
14 citations
All possible monothio analogues of the mono-, di-, and triethoxy homologues of mescaline have been synthesized and pharmacologically evaluated in man. Modifications at the ring position para to the ethylamine chain, either with a sulfur atom, a longer alkyl chain, or both, lead to compounds of high central nervous system activity. The 4-n-propoxy and 4-n-butoxy homologues and their...
Journal of Medicinal Chemistry
May 1, 1983
Peyton Jacob, Alexander T. Shulgin
18 citations
The two thio analogues of each of the well-known psychotomimetic drugs DOM [(2,5-dimethoxy-4-methylphenyl)isopropylamine] and DOET [(2,5-dimethoxy-4-ethylphenyl)isopropylamine] have been synthesized and pharmacologically evaluated in man. The 5-thio isomers are more potent as psychotomimetic agents than the 2-thio isomers but still represent a drop of an order of magnitude in potency from the...
Chemischer Informationsdienst
April 20, 1982
P. Iii Jacob, Alexander T. Shulgin
AbstractMonothioanaloga von Mescalin (I) und Isomescalin (II) werden dargestellt.
Journal of Medicinal Chemistry
November 1, 1981
Peyton Jacob, Alexander T. Shulgin
20 citations
Two monothio analogues of mescaline and three monothio analogues of 2,3,4-trimethoxyphenethylamine (isomescaline) have been synthesized and characterized. Only the two mescaline analogues (3-and 4-thiomescaline) were found to be psychotomimetics in man, being 6 and 12 times more potent than mescaline, respectively. All five compounds can serve as substrates for bovine plasma monoamine oxidase...
Journal of Medicinal Chemistry
February 1, 1980
Robert T. Standridge, Henry G. Howell, Hugh A. Tilson et al.
13 citations
A series of 2-amino-1-(4-substituted-2,5-dimethoxyphenyl)butanes (Table V) was prepared as analogues of (R)-2-amino-1-(2,5-dimethoxy-4-methylphenyl)butane (1a). 1-(2,5-Dimethoxyphenyl)-2-(N-phthalimido)butane (7) was utilized as a synthetic intermediate common to many of the target compounds. Animal data are presented indicating that most of these analogues have low hallucinogenic potential....
Journal of Pharmaceutical Sciences
July 1, 1979
Richard A Glennon, Lemont B. Kier, Alexander T. Shulgin
29 citations
The hallucinogenic (psychotomimetic) potency of 10 mescaline analogs was examined by molecular connectivity analysis. Potencies could be described by a two-term relating equation, which explained 94% of the variance in activity, on the basis of structural variation, 2,5-Dimethoxy substitution as well as the nature of the 4-position substituent played an important role in determining...
Journal of Psychedelic Drugs
1979
Alexander T. Shulgin
20 citations
(1979). Chemistry of Phenethylamines Related to Mescaline. Journal of Psychedelic Drugs: Vol. 11, Innovative Approached to Drug Abuse Treatment, pp. 41-52.
Journal of Labelled Compounds and Radiopharmaceuticals
1978
Gisela Braun, Alexander T. Shulgin, Thornton W. Sargent
9 citations
AbstractA rapid and convenient synthesis of the psychotomimetic agent 4‐iodo‐2, 5‐dimethoxyphenylisopropylamine is described, incorporating the radioisotope 123I (T1/2 13 hr). With the amine function of 2, 5‐dimethoxyphenylisopropylamine blocked as the phthalimide, it was found that the aromatic 4‐position could be directly iodinated with iodine monochloride. The phthalic acid moiety was...
Chemischer Informationsdienst
March 30, 1976
Alexander T. Shulgin, Donald C. Dyer
AbstractHydrochinondimethyläther (I) wird zu (IIa) und (IIb) acyliert.
Journal of Medicinal Chemistry
December 1, 1975
Alexander T. Shulgin, Donald C. Dyer
37 citations
A homologous series of 4-alkyl-2,5-dimethoxyphenylisopropylamines (alkyl = H through n-C5H11 and t-C4H9) was synthesized and compared with mescaline as serotonin agonists in a sheep umbilical preparation. The three-carbon homolog 6d was found to be the most potent of the straight-chain series in accordance with its observed psychotomimetic effectiveness in man.
Pharmacology
1973
Alexander T. Shulgin, Thornton W. Sargent, Carolina Lopez Naranjo
33 citations
A rationale is presented for the investigation of the synthesis and pharmacology of 3-methoxy-4,5-methylenedioxyphenyl isopropylamine (MMDA) as a potential psychodysleptic compound; these experiments are reported. The chemical synthesis and physical properties of this compound are described. The pharmacologic effects of MMDA in several animal species are presented, as are its clinical effects...
Pharmacology
1971
Alexander T. Shulgin, Thornton W. Sargent, C. Naranjo
A new centrally active halo-amine, 4-bromo-2,5 dimethoxyphenylisopropylamine, is described. In clinical evalua tion it proved to enhance effectively both emotional and in tellectual perception, without the imagery and perceptual distortions commonly encountered with many of the chemically related psychotomimetics. These properties suggest a potential valuable role in conjunction with...