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Author | Alexander and Ann Shulgin |
---|---|
Subject | Pharmacology, Autobiography, Psychoactive drugs |
Publisher | Transform Press |
Publication date | 1991 |
Publication place | United States |
Media type | Paperback |
ISBN | 0-9630096-0-5 |
OCLC | 269100404 |
Followed by | TiHKAL |
PiHKAL: A Chemical Love Story is a book by Alexander Shulgin and Ann Shulgin published in 1991. [1] [2] The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved".
The book is arranged into two parts, the first part being a fictionalized autobiography of the couple and the second part describing 179 different psychedelic compounds (most of which Shulgin discovered himself), including detailed synthesis instructions, bioassays, dosages, and other commentary.
The second part was made freely available by Shulgin on Erowid while the first part is available only in the printed text. While the reactions described are beyond the ability of people with a basic chemistry education, some tend to emphasize techniques that do not require difficult-to-obtain chemicals. Notable among these are the use of mercury-aluminum amalgam (an unusual but easy to obtain reagent) as a reducing agent and detailed suggestions on legal plant sources of important drug precursors such as safrole.
Through PIHKAL (and later TIHKAL ), Shulgin sought to ensure that his discoveries would escape the limits of professional research labs and find their way to the public, a goal consistent with his stated beliefs that psychedelic drugs can be valuable tools for self-exploration. The MDMA ("ecstasy") synthesis published in PIHKAL remains one of the most common clandestine methods of its manufacture to this day. Many countries have banned the major substances for which this book gives directions for synthesis, such as 2C-B, 2C-T-2, and 2C-T-7.
In 1994, two years after PIHKAL was published, the Drug Enforcement Administration (DEA) raided Shulgin's lab and requested that he turn over his DEA license. Richard Meyer, spokesman for DEA's San Francisco Field Division, has stated in reference to PIHKAL "It is our opinion that those books are pretty much cookbooks on how to make illegal drugs. Agents tell me that in clandestine labs that they have raided, they have found copies of those books", suggesting that the publication of PIHKAL and the termination of Shulgin's license may have been related. [3]
The "Essential Amphetamines" are what Shulgin describes as ten amphetamines that differ from natural products such as safrole or myristicin by an amine group (PIHKAL Entry #157 TMA). The list consists of:
Not all of these chemicals are bioassayed in PIHKAL; some are merely mentioned.
The so-called "magical half-dozen" refers to Shulgin's self-rated most important phenethylamine compounds, all of which except mescaline he developed and synthesized himself. They are found within the first book of PIHKAL, and are as follows:
All six are now Schedule I controlled substances in the United States. [4]
Substance | Chemical name | |
---|---|---|
1 | AEM | alpha-Ethyl-3,4,5-trimethoxy-PEA |
2 | AL | 4-Allyloxy-3,5-dimethoxy-PEA |
3 | ALEPH | 4-Methylthio-2,5-dimethoxy-A |
4 | ALEPH-2 | 4-Ethylthio-2,5-dimethoxy-A |
5 | ALEPH-4 | 4-Isopropylthio-2,5-dimethoxy-A |
6 | ALEPH-6 | 4-Phenylthio-2,5-dimethoxy-A |
7 | ALEPH-7 | 4-Propylthio-2,5-dimethoxy-A |
8 | ARIADNE (Dimoxamine) | 2,5-Dimethoxy-alpha-ethyl-4-methyl-PEA |
9 | ASB | 3,4-Diethoxy-5-methoxy-PEA |
10 | B | 4-Butoxy-3,5-dimethoxy-PEA |
11 | BEATRICE | 2,5-Dimethoxy-4,N-dimethyl-A |
12 | Bis-TOM | 2,5-Bismethylthio-4-methyl-A |
13 | BOB | 4-Bromo-2,5,beta-trimethoxy-PEA |
14 | BOD | 2,5,beta-Trimethoxy-4-methyl-PEA |
15 | BOH | beta-Methoxy-3,4-methylenedioxy-PEA |
16 | BOHD | 2,5-Dimethoxy-beta-hydroxy-4-methyl-PEA |
17 | BOM | 3,4,5,beta-Tetramethoxy-PEA |
18 | 4-Br-3,5-DMA | 4-Bromo-3,5-dimethoxy-A |
19 | 2-Br-4,5-MDA | 2-Bromo-4,5-methylenedioxy-A |
20 | 2C-B | 4-Bromo-2,5-dimethoxy-PEA |
21 | 3C-BZ | 4-Benzyloxy-3,5-dimethoxy-A |
22 | 2C-C | 4-Chloro-2,5-dimethoxy-PEA |
23 | 2C-D | 4-Methyl-2,5-dimethoxy-PEA |
24 | 2C-E | 4-Ethyl-2,5-dimethoxy-PEA |
25 | 3C-E | 4-Ethoxy-3,5-dimethoxy-A |
26 | 2C-F | 4-Fluoro-2,5-dimethoxy-PEA |
27 | 2C-G | 3,4-Dimethyl-2,5-dimethoxy-PEA |
28 | 2C-G-3 | 3,4-Trimethylene-2,5-dimethoxy-PEA |
29 | 2C-G-4 | 3,4-Tetramethylene-2,5-dimethoxy-PEA |
30 | 2C-G-5 | 3,4-Norbornyl-2,5-dimethoxy-PEA |
31 | 2C-G-N | 1,4-Dimethoxynaphthyl-2-ethylamine |
32 | 2C-H | 2,5-Dimethoxy-PEA |
33 | 2C-I | 4-Iodo-2,5-dimethoxy-PEA |
34 | 2C-N | 4-Nitro-2,5-dimethoxy-PEA |
35 | 2C-O-4 | 4-Isopropoxy-2,5-dimethoxy-PEA |
36 | 2C-P | 4-Propyl-2,5-dimethoxy-PEA |
37 | CPM | 4-Cyclopropylmethoxy-3,5-dimethoxy-PEA |
38 | 2C-Se | 4-Methylseleno-2,5-dimethoxy-PEA |
39 | 2C-T | 4-Methylthio-2,5-dimethoxy-PEA |
40 | 2C-T-2 | 4-Ethylthio-2,5-dimethoxy-PEA |
41 | 2C-T-4 | 4-Isopropylthio-2,5-dimethoxy-PEA |
42 | psi-2C-T-4 | 4-Isopropylthio-2,6-dimethoxy-PEA |
43 | 2C-T-7 | 4-Propylthio-2,5-dimethoxy-PEA |
44 | 2C-T-8 | 4-Cyclopropylmethylthio-2,5-dimethoxy-PEA |
45 | 2C-T-9 | 4-(t)-Butylthio-2,5-dimethoxy-PEA |
46 | 2C-T-13 | 4-(2-Methoxyethylthio)-2,5-dimethoxy-PEA |
47 | 2C-T-15 | 4-Cyclopropylthio-2,5-dimethoxy-PEA |
48 | 2C-T-17 | 4-(s)-Butylthio-2,5-dimethoxy-PEA |
49 | 2C-T-21 | 4-(2-Fluoroethylthio)-2,5-dimethoxy-PEA |
50 | 4-D | 4-Trideuteromethyl-3,5-dimethoxy-PEA |
51 | beta-D | beta,beta-Dideutero-3,4,5-trimethoxy-PEA |
52 | DESOXY | 4-Methyl-3,5-Dimethoxy-PEA |
53 | 2,4-DMA | 2,4-Dimethoxy-A |
54 | 2,5-DMA | 2,5-Dimethoxy-A |
55 | 3,4-DMA | 3,4-Dimethoxy-A |
56 | DMCPA | 2-(2,5-Dimethoxy-4-methylphenyl)-cyclopropylamine |
57 | DME | 3,4-Dimethoxy-beta-hydroxy-PEA |
58 | DMMDA | 2,5-Dimethoxy-3,4-methylenedioxy-A |
59 | DMMDA-2 | 2,3-Dimethoxy-4,5-methylenedioxy-A |
60 | DMPEA | 3,4-Dimethoxy-PEA |
61 | DOAM | 4-Amyl-2,5-dimethoxy-A |
62 | DOB | 4-Bromo-2,5-dimethoxy-A |
63 | DOBU | 4-Butyl-2,5-dimethoxy-A |
64 | DOC | 4-Chloro-2,5-dimethoxy-A |
65 | DOEF | 4-(2-Fluoroethyl)-2,5-dimethoxy-A |
66 | DOET | 4-Ethyl-2,5-dimethoxy-A |
67 | DOI | 4-Iodo-2,5-dimethoxy-A |
68 | DOM (STP) | 4-Methyl-2,5-dimethoxy-A |
69 | Psi-DOM | 4-Methyl-2,6-dimethoxy-A |
70 | DON | 4-Nitro-2,5-dimethoxy-A |
71 | DOPR | 4-Propyl-2,5-dimethoxy-A |
72 | E | 4-Ethoxy-3,5-dimethoxy-PEA |
73 | EEE | 2,4,5-Triethoxy-A |
74 | EEM | 2,4-Diethoxy-5-methoxy-A |
75 | EME | 2,5-Diethoxy-4-methoxy-A |
76 | EMM | 2-Ethoxy-4,5-dimethoxy-A |
77 | ETHYL-J | N,alpha-diethyl-3,4-methylenedioxy-PEA |
78 | ETHYL-K | N-Ethyl-alpha-propyl-3,4-methylenedioxy-PEA |
79 | F-2 | Benzofuran-2-methyl-5-methoxy-6-(2-aminopropane) |
80 | F-22 | Benzofuran-2,2-dimethyl-5-methoxy-6-(2-aminopropane) |
81 | FLEA | N-Hydroxy-N-methyl-3,4-methylenedioxy-A |
82 | G-3 | 3,4-Trimethylene-2,5-dimethoxy-A |
83 | G-4 | 3,4-Tetramethylene-2,5-dimethoxy-A |
84 | G-5 | 3,4-Norbornyl-2,5-dimethoxy-A |
85 | GANESHA | 3,4-Dimethyl-2,5-dimethoxy-A |
86 | G-N | 1,4-Dimethoxynaphthyl-2-isopropylamine |
87 | HOT-2 | 2,5-Dimethoxy-N-hydroxy-4-ethylthio-PEA |
88 | HOT-7 | 2,5-Dimethoxy-N-hydroxy-4-(n)-propylthio-PEA |
89 | HOT-17 | 2,5-Dimethoxy-N-hydroxy-4-(s)-butylthio-PEA |
90 | IDNNA | 2,5-Dimethoxy-N,N-dimethyl-4-iodo-A |
91 | IM | 2,3,4-Trimethoxy-PEA |
92 | IP | 3,5-Dimethoxy-4-isopropoxy-PEA |
93 | IRIS | 5-Ethoxy-2-methoxy-4-methyl-A |
94 | J | alpha-Ethyl-3,4-methylenedioxy-PEA |
95 | LOPHOPHINE | 3-Methoxy-4,5-methylenedioxy-PEA |
96 | M | 3,4,5-Trimethoxy-PEA |
97 | 4-MA (PMA) | 4-Methoxy-A |
98 | MADAM-6 | 2,N-Dimethyl-4,5-methylenedioxy-A |
99 | MAL | 3,5-Dimethoxy-4-methallyloxy-PEA |
100 | MDA | 3,4-Methylenedioxy-A |
101 | MDAL | N-Allyl-3,4-methylenedioxy-A |
102 | MDBU | N-Butyl-3,4-methylenedioxy-A |
103 | MDBZ | N-Benzyl-3,4-methylenedioxy-A |
104 | MDCPM | N-Cyclopropylmethyl-3,4-methylenedioxy-A |
105 | MDDM | N,N-Dimethyl-3,4-methylenedioxy-A |
106 | MDE | N-Ethyl-3,4-methylenedioxy-A |
107 | MDHOET | N-(2-Hydroxyethyl)-3,4-methylenedioxy-A |
108 | MDIP | N-Isopropyl-3,4-methylenedioxy-A |
109 | MDMA | N-Methyl-3,4-methylenedioxy-A |
110 | MDMC (EDMA) | N-Methyl-3,4-ethylenedioxy-A |
111 | MDMEO | N-Methoxy-3,4-methylenedioxy-A |
112 | MDMEOET | N-(2-Methoxyethyl)-3,4-methylenedioxy-A |
113 | MDMP | alpha,alpha,N-Trimethyl-3,4-methylenedioxy-PEA |
114 | MDOH | N-Hydroxy-3,4-methylenedioxy-A |
115 | MDPEA | 3,4-Methylenedioxy-PEA |
116 | MDPH | alpha,alpha-Dimethyl-3,4-methylenedioxy-PEA |
117 | MDPL | N-Propargyl-3,4-methylenedioxy-A |
118 | MDPR | N-Propyl-3,4-methylenedioxy-A |
119 | ME | 3,4-Dimethoxy-5-ethoxy-PEA |
120 | MEDA | 3-methoxy-4,5-Ethylenedioxy-A [Erowid corrected] |
121 | MEE | 2-Methoxy-4,5-diethoxy-A |
122 | MEM | 2,5-Dimethoxy-4-ethoxy-A |
123 | MEPEA | 3-Methoxy-4-ethoxy-PEA |
124 | Meta-DOB | 5-Bromo-2,4-dimethoxy-A |
125 | Meta-DOT | 5-Methylthio-2,4-dimethoxy-A |
126 | Methyl-DMA | N-Methyl-2,5-dimethoxy-A |
127 | Methyl-DOB | 4-Bromo-2,5-dimethoxy-N-methyl-A |
128 | Methyl-J | N-Methyl-alpha-ethyl-3,4-methylenedioxy-PEA |
129 | Methyl-K | N-Methyl-alpha-propyl-3,4-methylenedioxy-PEA |
130 | Methyl-MA | N-Methyl-4-methoxy-A |
131 | Methyl-MMDA-2 | N-Methyl-2-methoxy-4,5-methylenedioxy-A |
132 | MMDA | 3-Methoxy-4,5-methylenedioxy-A |
133 | MMDA-2 | 2-Methoxy-4,5-methylenedioxy-A |
134 | MMDA-3a | 2-Methoxy-3,4-methylenedioxy-A |
135 | MMDA-3b | 4-Methoxy-2,3-methylenedioxy-A |
136 | MME | 2,4-Dimethoxy-5-ethoxy-A |
137 | MP | 3,4-Dimethoxy-5-propoxy-PEA |
138 | MPM | 2,5-Dimethoxy-4-propoxy-A |
139 | Ortho-DOT | 2-Methylthio-4,5-dimethoxy-A |
140 | P | 3,5-Dimethoxy-4-propoxy-PEA |
141 | PE | 3,5-Dimethoxy-4-phenethyloxy-PEA |
142 | PEA | PEA |
143 | PROPYNYL | 4-Propynyloxy-3,5-dimethoxy-PEA |
144 | SB | 3,5-Diethoxy-4-methoxy-PEA |
145 | TA | 2,3,4,5-Tetramethoxy-A |
146 | 3-TASB | 4-Ethoxy-3-ethylthio-5-methoxy-PEA |
147 | 4-TASB | 3-Ethoxy-4-ethylthio-5-methoxy-PEA |
148 | 5-TASB | 3,4-Diethoxy-5-methylthio-PEA |
149 | TB | 4-Thiobutoxy-3,5-dimethoxy-PEA |
150 | 3-TE | 4-Ethoxy-5-methoxy-3-methylthio-PEA |
151 | 4-TE | 3,5-Dimethoxy-4-ethylthio-PEA |
152 | 2-TIM | 2-Methylthio-3,4-dimethoxy-PEA |
153 | 3-TIM | 3-Methylthio-2,4-dimethoxy-PEA |
154 | 4-TIM | 4-Methylthio-2,3-dimethoxy-PEA |
155 | 3-TM | 3-Methylthio-4,5-dimethoxy-PEA |
156 | 4-TM | 4-Methylthio-3,5-dimethoxy-PEA |
157 | TMA | 3,4,5-Trimethoxy-A |
158 | TMA-2 | 2,4,5-Trimethoxy-A |
159 | TMA-3 | 2,3,4-Trimethoxy-A |
160 | TMA-4 | 2,3,5-Trimethoxy-A |
161 | TMA-5 | 2,3,6-Trimethoxy-A |
162 | TMA-6 | 2,4,6-Trimethoxy-A |
163 | 3-TME | 4,5-Dimethoxy-3-ethylthio-PEA |
164 | 4-TME | 3-Ethoxy-5-methoxy-4-methylthio-PEA |
165 | 5-TME | 3-Ethoxy-4-methoxy-5-methylthio-PEA |
166 | 2T-MMDA-3a | 2-Methylthio-3,4-methylenedioxy-A |
167 | 4T-MMDA-2 | 4,5-Thiomethyleneoxy-2-methoxy-A |
168 | TMPEA | 2,4,5-Trimethoxy-PEA |
169 | 2-TOET | 4-Ethyl-5-methoxy-2-methylthio-A |
170 | 5-TOET | 4-Ethyl-2-methoxy-5-methylthio-A |
171 | 2-TOM | 5-Methoxy-4-methyl-2-methylthio-A |
172 | 5-TOM | 2-Methoxy-4-methyl-5-methylthio-A |
173 | TOMSO | 2-Methoxy-4-methyl-5-methylsulfinyl-A |
174 | TP | 4-Propylthio-3,5-dimethoxy-PEA |
175 | TRIS | 3,4,5-Triethoxy-PEA |
176 | 3-TSB | 3-Ethoxy-5-ethylthio-4-methoxy-PEA |
177 | 4-TSB | 3,5-Diethoxy-4-methylthio-PEA |
178 | 3-T-TRIS | 4,5-Diethoxy-3-ethylthio-PEA |
179 | 4-T-TRIS | 3,5-Diethoxy-4-ethylthio-PEA |
2C-T-7 is a psychedelic phenethylamine of the 2C family. In his book PiHKAL: A Chemical Love Story, Alexander Shulgin lists the dosage range as 10–30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic effects that last 8 to 15 hours. Up until Operation Web Tryp and three deaths, two of which involved the use of other drugs in addition to 2C-T-7, and one which involved an excessive insufflated dose, 2C-T-7 was sold commercially in Dutch and Japanese smartshops and online. It is known on the streets as Blue Mystic or 7th Heaven. There has been little real research done on this chemical other than Shulgin's comments in PiHKAL and a few small animal studies mostly aimed at detecting metabolites.
2,4,5-Trimethoxyamphetamine (2,4,5-TMA), also known as TMA-2 or as 2,5-dimethoxy-4-methoxyamphetamine (DOMeO), is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the trimethoxyamphetamine (TMA) series of positional isomers. The drug is also notable in being the 4-methoxylated member of the DOx series of drugs.
Trimethoxyamphetamine, also known as 3,4,5-trimethoxyamphetamine (3,4,5-TMA), α-methylmescaline, or mescalamphetamine, is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the trimethoxyamphetamine (TMA) series of positional isomers. The drug is notable in being the amphetamine analogue of mescaline (3,4,5-trimethoxyphenethylamine).
Trimethoxyamphetamines (TMAs) are a family of positionally isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the positions of the three methoxy groups: TMA (TMA-1), TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are substituted amphetamines and are analogues of the phenethylamine cactus alkaloid mescaline and the DOx drugs.
2C-G is a psychedelic phenethylamine of the 2C-series. First synthesized by Alexander Shulgin, it is sometimes used as an entheogen. It has structural and pharmacodynamic properties similar to 2C-D and Ganesha. Like many of the phenethylamines in PiHKAL, 2C-G and its homologs have only been taken by Shulgin and a small test group, making it difficult to ensure completeness when describing effects.
2,5-Dimethoxy-4-chloroamphetamine (DOC) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was presumably first synthesized by Alexander Shulgin, and was described in his book PiHKAL.
2C-T is a psychedelic and hallucinogenic drug of the 2C family. It is used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and 2C-T-2.
2,5-Dimethoxy-4-ethylamphetamine (DOET) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is closely related to DOM and is a synthetic analogue of the naturally occurring phenethylamine psychedelic mescaline. The drug acts as a selective agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.
MMDA is a psychedelic and entactogen drug of the amphetamine class. It is an analogue of lophophine, MDA, and MDMA.
DMMDA-2 is a bioactive phenethylamine discussed by Alexander Shulgin in his book PiHKAL ; however, he was not the first to synthesize it. Shulgin comments in his book that a 50 milligram dose of DMMDA-2 produces similar effects to 3,4-methylenedioxy-1-α-methylphenylethylamine. DMMDA-2 can be synthesized from dillapiole.
2C (2C-x) is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolically stable and longer acting compounds.
Ganesha (2,5-dimethoxy-3,4-dimethylamphetamine) is a lesser-known psychedelic drug. It is also a substituted amphetamine. It was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 24–32 mg. The drug is usually taken orally, although other routes such as rectally may also be used. Ganesha is synthesized from 2,5-dimethoxy-3,4-dimethylbenzaldehyde. Ganesha is the amphetamine analog of 2C-G. It is a particularly long lasting drug, with the duration listed in PiHKAL as being 18–24 hours, which might make it undesirable to some users. It is named after the Hindu deity, Ganesha. Very little is known about the dangers or toxicity of ganesha. Effects of ganesha include:
3,4-Dimethoxyphenethylamine (DMPEA) is a chemical compound of the phenethylamine class. It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups. It is also closely related to mescaline which is 3,4,5-trimethoxyphenethylamine and to 3,4-dimethoxyamphetamine (3,4-DMA).
Dimethoxyamphetamine (DMA) is a series of six lesser-known psychedelic drugs similar in structure to the three isomers of methoxyamphetamine and six isomers of trimethoxyamphetamine. The isomers are 2,3-DMA, 2,4-DMA, 2,5-DMA, 2,6-DMA, 3,4-DMA, and 3,5-DMA. Three of the isomers were characterized by Alexander Shulgin in his book PiHKAL. Little is known about their dangers or toxicity.
2,5-Dimethoxy-3,4-methylenedioxy-1-α-methylphenylethylamine is a lesser-known bioactive derivative compound of the phenethylamine and α-methylphenylethylamine chemical classes. It was first synthesized by Alexander Shulgin and was described in his book PiHKAL. Shulgin listed the dosage as 30–75 mg and the duration as 6–8 hours. He reported DMMDA as producing D-lysergic acid diethylamide-like subjective effects: images, mydriasis, ataxia, and time dilation. DMMDA is not mentioned much in literature outside PiHKAL unlike 2,5-dimethoxy-4-bromo-1-phenylethylamine.
Trimethoxyphenethylamines (TMPEA) are a group of positional isomers of the psychedelic cactus alkaloid mescaline. Some of them are described in the book PiHKAL by Alexander Shulgin and Ann Shulgin.
MMDA-2 (2-methoxy-4,5-methylenedioxyamphetamine) is a psychedelic drug of the amphetamine class. It is closely related to MMDA and MDA.
N-Methyl-2-methoxy-4,5-methylenedioxyamphetamine is a psychedelic drug of the amphetamine class. It is the N-methylated derivative of MMDA-2, and it is also an analog of MDMA and 6-methyl-MDA.
4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. They are 4-substituted derivatives of 2,5-dimethoxyamphetamine.
3,4-Dimethoxyamphetamine (3,4-DMA), or simply dimethoxyamphetamine (DMA), is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers.