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N-Methyl Hallucinogenic Amphetamine Analysis

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Rhodium:
Identification of the N-Methylated Analogs of the Hallucinogenic Amphetamines
K. Bailey, A.W. By,
Journal of the Association of Official Analytical Chemists, 56(1), 62-69 (1975) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/n-methyl-amphetamines.pdf)

Abstract
The drugs 2-, 3-, and 4-methoxy-N-methylamphetamine, 3-methoxy-4,5-methylenedioxy-N-methylamphetamine and 3,4-methylenedioxy-N-methylamphetamine are identified by spectroscopic techniques. The ultraviolet and mass spectra of isomers are similar, but proton magnetic resonance and infrared spectra are distinctly different, and reference spectra and data are provided. Gas-liquid and thin layer chromatographic systems for the analysis are discussed.

Islamybad:
Did you see these?

dimethoxyamphetamines
Journal of the AOAC Vol. 57 pages 70-78 (1974)

brominated dimethoxyamphetamines
Journal of the AOAC Vol. 59 pages 1162-1169 (1976)

methoxy and methylamphetamines
Journal of the AOAC Vol. 57 pages 1134-1143 (1974)

MDA, 3,4-MDphenylnitropropene, MDP2P, etc.
Journal of the AOAC Vol. 61 pages 951-967 (1978)

Islamybad:
Here's the IR spectrum of myristicin from two sources:

http://www.geocities.com/milkmandan2003/myristicinIR.html

Rhodium:
Gas Chromatographic-Mass Spectrometric and Liquid Chromatographic Analysis of Designer Butanamines Related to MDMA
C. Randall Clark, Jack DeRuiter, Allen Valaer, F. Taylor Noggle
Journal of Chromatographic Science, Vol. 33, 328-337 (1995) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/designer.mdma.butanamines.pdf)

Abstract
A series of N-substituted, 1-(3,4-methylenedioxyphenyl)-2-butanamines (MDP-2-B) is prepared from piperonal via the 2-butanone intermediate. The analytical properties of these compounds are compared with the structurally similar 3,4-methylenedioxyamphetamine (MDA) derivatives, a popular series of drugs of abuse. The ultraviolet absorption properties of these compounds are determined by the methylenedioxyphenyl ring, which shows major absorption bands in the 285- and 235-nm range. The primary amine (MDP-2-B) and the N-substituted derivatives of MDP-2-B are separated by reversed-phase liquid chromatography under acidic mobile-phase conditions. The compounds are not completely resolved by gas chromatography on an HP-1 phase, and the separation is complicated by extensive thermal degradation of the N-hydroxy derivative (MDP-2-OHB). The mass spectra for these compounds provide specific structural information for the identification of these compounds. The amines undergo -cleavage reactions to produce ions at [M-135]+ from the loss of the 3,4-methylenedioxybenzyl radical and [M-29]+ from loss of the other -group, the ethyl radical.
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Liquid Chromatographic and Mass Spectral Analysis of 1-(3,4-Methylenedioxyphenyl)-3-butanamines, Homologues of 3,4-Methylenedioxyamphetamines
F. Taylor Noggle, Jr., C. Randall Clark and Jack DeRuiter
Journal of Chromatographic Science, Vol. 27, 240-243 (1989) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/noggle.mdp-3-butanamines.pdf)

Abstract
The 1-(3,4-methylenedioxyphenyl)-3-butanamines (HMDAs) are prepared via reductive amination of the corresponding ketone with a series of low molecular weight alkylamines. These amines are homologues of the N-substituted 3,4-methylenedioxyamphetamines (MDAs). Compounds of the HMDA series have UV absorption properties similar to the MDAs because both series contain the same 3,4-methylenedioxyphenyl chromophore. The HMDAs are separated via reversed-phase liquid chromatographic methods using a C,0 stationary phase and an acidic aqueous acetonitrile mobile phase. The mass spectra of these potential designer drugs are very similar to the spectra of the MDA homologues having the same N-substituent.
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Chromatographic and Spectroscopic Methods of Identification for the Side-Chain Regioisomers of 3,4-Methylenedioxyphenethylamines Related to MDEA, MDMMA, and MBDB
Laura Aalberg, Jack DeRuiter, F. Taylor Noggle, Erkki Sippola, and C. Randall Clark
Journal of Chromatographic Science, Vol. 41, 227-233 (2003) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/mdea-mdmma-mbdb.regioisomers.pdf)

Abstract
Three regioisomeric 3,4-methylenedioxyphenethylamines having the same molecular weight and major mass spectral fragments of equivalent mass have been reported as components of clandestine drug samples in recent years. These drugs of abuse are 3,4-methylenedioxy-N-ethylamphetamine, 3,4-methylenedioxy-N, N-dimethylamphetamine, and N-methyl-1 -(3,4-methylenedioxyphenyl)-2-butanamine. These three compounds are a subset of a total of ten regioisomeric 3,4-methylenedioxyphenethylamines of molecular weight 207, yielding regioisomeric fragment ions of equivalent mass (m/z 72 and 135/136) in the electron impact mass spectrum. The specific identification of one of these compounds in a forensic drug sample depends upon the analyst's ability to eliminate the other regioisomers as possible interfering or coeluting substances. This paper reports the synthesis, mass spectral characterization, and chromatographic analysis of these ten unique regioisomers. The ten regioisomeric methylenedioxyphenethylamines are synthesized from commercially available precursor chemicals. The electron impact mass spectra of these regioisomers show some variation in the relative intensity of the major ions with only one or two minor ions that might be considered side-chain specific fragments. Thus, the ultimate identification of any one of these amines with the elimination of the other nine regioisomeric substances depends heavily upon chromatographic methods. Chromatographic separation of these ten uniquely regioisomeric amines is studied using gas chromatographic temperature program optimization.
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Liquid Chromatographic and Mass Spectral Analysis of 1-(3,4-Methylenedioxyphenyl)-1-propanamines: Regioisomers of the 3,4-Methylenedioxyamphetamines
Jack DeRuiter, C. Randall Clark and F. Taylor Noggle, Jr.
Journal of Chromatographic Science, Vol. 28,  129-132 (1990) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/mda.alpha-analogs.pdf)

Abstract
The title 1-(3,4-methylenedioxyphenyl)-1-propanamines represent positional isomers of the N-substituted 3,4-methylenedioxyamphetamines, clandestinely produced drugs frequently encountered by forensic laboratories. These propanamines are prepared by reductive amination of 3,4-methylenedioxypropiophenone with a series of N-alkylamines. Analytical methods are developed to distinguish these compounds from the MDA series. The ultraviolet spectra of the propanamines are very similar to those of the MDAs with absorption maxima at 284 and 236 nm. The propanamines are separated under reversed-phase liquid chromatographic conditions by using a C18 stationary phase and a mobile phase of acidic (pH 3) acetonitrile containing methanol and triethylamine. The relative retention properties of these compounds parallel those observed in the MDA series. The electron impact mass spectra of the propanamines are determined by GC-MS, and the fragmentation pattern clearly distinguishes these compounds from those of the MDA series having the same molecular weight.
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Liquid Chromatographic and Mass Spectral Analysis of 1-(3,4-Methylenedioxyphenyl)-3-Propanamines: Regioisomers of MDMA
F. Taylor Noggle, Jr., C. Randall Clark, Kamal H. Bouhadir and Jack DeRuiter
Journal of Chromatographic Science, Vol. 29, 78-82 (1991) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/mdma.3-propanamines.pdf)

Abstract
The 1-(3,4-methylenedioxyphenyl)-3-propanamines are prepared from 1-(3,4-methylenedioxyphenyl)propanoic acid via amide formation followed by hydride reduction. The 3-propanamines are regioisomeric with the 1-(3,4-methylenedioxyphenyl)-2-propanamines MDA and MDMA, a series of popular drugs of abuse. The N-substituted 3-propanamines were separated via reversed-phase liquid chromatography (LC) using an acidic mobile phase (pH 3). Similar reversed-phase conditions were used to separate the N-methyl derivatives of the regioisomeric 1-, 2-, and 3-propanamines. The electron impact (EI) mass spectra for the 3-propanamines show the characteristic amine base peak and can be used to differentiate these compounds from the regioisomeric 2-propanamines.
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Methods for the Analysis of 1-(3,4-Methylenedioxyphenyl)-2-Butanamine and N-Methyl-1-(3,4-Methylenedioxyphenyl)-2-Propanamine (MDMA)
F. Taylor Noggle, Jr., C. Randall Clark, Shridhar Andurkar, and Jack DeRuiter
Journal of Chromatographic Science, Vol 29, 103-106 (1991) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/mdma-bdb.analysis.pdf)

Abstract
The infrared and mass spectra of N-methyl-1-(3,4-methylenedioxyphenyl)-2-propanamine (MDMA) and 1-(3,4-methylenedioxyphenyl)-2-butanamine are quite similar. These two compounds differ only in the position of substitution of a single methyl group. MDMA is a controlled street drug known as Ecstasy, while the isomeric butanamine is a member of a new class of potential psychotherapeutic agents called entactogens. These two compounds produce similar mass spectral fragmentation patterns including a common base peak at m/z 58. Reversed-phase liquid chromatographic (RPLC) methods consisting of a C18 stationary phase and an aqueous acidic mobile phase were used to separate these two compounds. Thus, LC methods can be used to differentiate MDMA from the isomeric butanamine for forensic analysis.
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Liquid Chromatographic and Mass Spectral Analysis of N-Substituted Analogues of 3,4-Methylenedioxyamphetamine
F. Taylor Noggle, Jr., C. Randall Clark, Alan K. Valaer, and Jack DeRuiter
Journal of Chromatographic Science, Vol. 26, 410-415 (1988) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/n-alkyl-mda.analysis.pdf)

Abstract
The C1 to C3 N-alkyl, N,N-dimethyl, and N-hydroxy analogues of 3,4-methylenedioxyamphetamine (MDA) are identified by high performance liquid chromatographic (HPLC) and spectrometric techniques. The compounds are separated using reversed-phase procedures on C18 stationary phase with an acidic (pH 3) aqueous methanol mobile phase. The mass spectra of the compounds are distinctive and reference spectra are provided. The N-hydroxy derivative is unstable at high temperatures and decomposes to MDA and the oxime of 3,4-methylenedioxyphenyl-2-propanone.

Rhodium:
Note that no yields are given, and that the chromatograms of their 'products' are highly impure. These papers are not to be taken as descriptions of a working procedure.

Gas Chromatographic and Mass Spectrometric Analysis of Samples from a Clandestine Laboratory Involved in the Synthesis of Ecstacy from Sassafras Oil
F.T. Noggle, Jr., C. Randall Clark and Jack DeRuiter
Journal of Chromatographic Science, Vol. 29, 168-173 (1991) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/noggle.sassy2mdma-1.pdf)

Abstract
The various samples from a clandestine drug laboratory reported to be involved in the synthesis of 3,4-methylenedioxymethamphetamine (MDMA, Ecstacy, or XTC) are analyzed by gas chromatography–mass spectrometry (GC–MS). Safrole, the starting material for the synthesis, is obtained from the roots of the sassafras plant. GC–MS of the sassafras oil reveals the presence of safrole (4-allyl-1,2-methylenedioxybenzene) as the major component, as well as smaller quantities of camphor, eugenol, a dimethoxyallyl- and trimethoxyallylbenzene. A second sample obtained from the clandestine laboratory is from the treatment of the sassafras oil with HBr. Although this sample contains many brominated and several nonbrominated components, the major constituent is the synthetic precursor for MDMA, 1-(3,4-methylenedioxyphenyl)-2-bromopropane, along with quantities of the regioisomeric 3-bromopropane. The samples from the clandestine laboratory do not reveal the presence of any MDMA. However, upon treatment with methylamine, the brominated sassafras oil gives MDMA as the major amine product.
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Gas Chromatographic and Mass Spectrometric Analysis of N-Methyl-1-Aryl-2-Propanamines Synthesized from the Substituted Allylbenzenes Present in Sassafras Oil
F.T. Noggle, Jr., C. Randall Clark and Jack DeRuiter
Journal of Chromatographic Science, Vol 29, 267-271 (1991) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/noggle.sassy2mdma-2.pdf)

Abstract
One method used for the synthesis of the illicit drug N-methyl-1-(3,4-methylenedioxyphenyl)-2-propanamine (methylenedioxymethamphetamine, MDMA) involves the treatment of safrole with HBr to form the intermediate 2-bromosafrole, followed by bromide displacement with methylamine. The starting material required for this synthesis, safrole, may be obtained from sassafras oil which is isolated from the roots of the sassafras plant. In addition to safrole, sassafras oil contains other allylbenzenes such as eugenol and 4-allyl-1,2-dimethoxybenzene. Gas chromatography–mass spectrometric (GC–MS) studies show that these allylbenzenes may also be brominated and undergo amine displacement to yield the corresponding N-methyl-1-aryl-2-propanamines. These studies also show that the regioisomeric 3-bromosafrole intermediate and 3-propanamine are not formed during this synthesis. Furthermore, the isomeric allylbenzenes isosaf role and isoeugenol that are generated in these reactions do not form stable bromo products and therefore no N-methyl-1-aryl-1-propanamine products are produced during the course of the bromination and amine displacement reactions.
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Analysis of 1-(3-Methoxy-4,5-Methylenedioxyphenyl)-2-Propanamine (MMDA) Derivatives Synthesized from Nutmeg Oil and 3-Methoxy-4,5-Methylenedioxybenzaldehyde
C. Randall Clark, F. Taylor Noggle and Jack DeRuiter
Journal of Chromatographic Science, Vol. 34, 34-42 (1996) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/mmda.nutmeg.pdf)

Abstract
Myristicin, a natural product found in nutmeg oil and nutmeg extract, contains the carbon skeleton for a series of drugs of abuse related to the 3,4-methylenedioxyamphetamines (MDAs). Myristicin, 1-(3-methoxy-4,5-methylenedioxyphenyl)-2-propene, was identified as the major component of commercially available nutmeg oil and in the organic extract of nutmeg powder. The starting materials, intermediates, and products in the synthesis of the drug of abuse N-methyl-1-(3-methoxy-4,5-methylenedioxyphenyl)-2-propanamine (MMDMA) from myristicin were characterized by gas chromatographic-mass spectrometric analysis. MMDMA and several primary amine derivatives including 1-(3-methoxy-4,5-methylenedioxyphenyl)-2-ethanamine, -propanamine, and -butanamine were also prepared from the commercially available aldehyde, 3-methoxy-4,5-methylenedioxybenzaldehyde. Each of these amine derivatives has a distinct mass spectrum characterized by amine-dominated fragmentation. All four amines in this study were resolved by reversed-phase liquid chromatography using an acidic aqueous mobile phase. Relative retention in this system was determined by differences in the hydrophobic surface area of the four amines.

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