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#94 J


[3D .mol structure]
SYNTHESIS: The Grignard reagent of propyl bromide was made by the dropwise addition of 52 g 1-bromopropane to a stirred suspension of 14 g magnesium turnings in 50 mL anhydrous Et2O. After the addition, stirring was continued for 10 min, and then a solution of 50 g piperonal in 200 mL anhydrous Et2O was added over the course of 30 min. The reaction mixture was heated at reflux for 8 h, then cooled with an external ice bath. It was quenched with the addition of a solution of 75 mL cold, saturated aqueous ammonium chloride. The formed solids were removed by filtration, and the two-phase filtrate separated. The organic phase was washed with 3x200 mL dilute HCl, dried over anhydrous MgSO4, and the solvent removed under vacuum. The crude 62.2 g of 1-(3,4-methylenedioxyphenyl)-2-butanol, which contained a small amount of the olefin that formed by dehydration, was distilled at 98 °C at 0.07 mm/Hg to give an analytical sample, but the crude isolate served well in the next reaction. Anal. (C11H14O3) C,H.

A mixture of 65 g crude 1-(3,4-methylenedioxyphenyl)-2-butanol and 1 g finely powdered potassium bisulfate was heated with a soft flame until the internal temperature reached 170 °C and H2O was no longer evolved. The entire reaction mixture was then distilled at 100-110 °C at 0.8 mm/Hg to give 55 g of 1-(3,4-methylenedioxyphenyl)-1-butene as a colorless oil. Anal. (C11H12O2) C,H.

To 240 mL of stirred and cooled formic acid there was added 30 mL H2O followed, slowly, by 45 mL of 35% hydrogen peroxide. There was then added a solution of 48 g 1-(3,4-methylenedioxyphenyl)-1-butene in 240 mL acetone at a rate that maintained the internal temperature at less than 40 °C. After the addition, the reaction mixture was allowed to stand and stir for several additional days. The excess volatiles were removed under vacuum with the temperature never allowed to exceed 40 °C. The residue was dissolved in 90 mL MeOH and diluted with 450 mL 15% H2SO4. This mixture was heated on the steam bath for 2.5 h, cooled, and then extracted with 3x100 mL Et2O. The extracts were pooled, washed with 2x200 mL H2O, 2x200 mL 5% NaOH, 2x200 mL brine, and then dried over anhydrous MgSO4. After removal of the solvent under vacuum, the residue was distilled at 105-135 °C at 0.3 mm/Hg to give 28.2 g 1-(3,4-methylenedioxyphenyl)-2-butanone as an amber oil. Redistillation gave a colorless oil, with a bp of 98 °C at 0.11 mm/Hg. Anal. (C11H12O3) C,H. This intermediate ketone could be prepared by the Wittig reaction between piperonal and the derivative of triphenylphosphonium propyl bromide and dibutyldisulfide, followed by hydrolysis in a HCl/acetic acid mixture, but the yields were no better, Efforts to prepare this ketone by the iron and acid reduction of the appropriate nitrostyrene (1-(3,4-methylenedioxyphenyl)-2-nitro-1-butene, mp 64-65 °C) were thwarted by the consistently unsatisfactory yield of the precursor from the reaction between piperonal and 1-nitropropane.

A stirred solution of 20 g anhydrous ammonium acetate and 4.6 g 1-(3,4-methylenedioxyphenyl)-2-butanone in 50 mL MeOH was treated with 1.57 g sodium cyanoborohydride. Droplets of HCl were added as needed to maintain the pH at approximately 6. The reaction mixture was made basic with the addition of 250 mL dilute NaOH and extracted with 3x100 mL CH2Cl2. The pooled organic extracts were extracted with 2x100 mL dilute H2SO4, the pooled aqueous extracts made basic again, and extracted again with 2x100 mL CH2Cl2. Removal of the solvent gave a residue which was distilled to give 2.6 g of a colorless oil which was dissolved in 15 mL IPA, neutralized with concentrated HCl, and diluted with an equal volume of anhydrous Et2O. Crystals of 2-amino-1-(3,4-methylenedioxyphenyl)butane hydrochloride (J) separated slowly. After filtering, Et2O washing, and air drying there was obtained 2.8 g of white crystals that melted at 159-161 °C. Anal. (C11H16ClNO2) C,H,N.

DOSAGE: 150 - 230 mg.

DURATION: 4 - 8 h.

QUALITATIVE COMMENTS: (with 175 mg) The first stirrings were evident in a half hour, pleasant feelings, and without any untoward body effects. Within another half hour I was at a plus 2 and there it leveled off. I would be reluctant to drive a car, but I could were it necessary. There were no visual distortions, no giddiness, no introspective urges, and no rise to a psychedelic intoxication of any significance. After about an hour and a half at this level, I gradually dropped back over another two hours. Afterwards I was quite fatigued and languorous.

(with 200 mg and a 75 mg supplement) RA very strong climb, and a very good, interior feeling. It has some of the MDMA properties, but it is difficult to concentrate on any one point. There is a tendency to slide off. Excellent emotional affect; music is fine but not gripping. Someone had used the phrase, mental nystagmus, and there is something valid there. The supplement was taken at the 2 hour point when I was already aware of some dropping, and its action was noticed in about a half hour.

(with 230 mg) Physically, there was a bit of dry mouth but no teeth clenching, some nystagmus, maybe the slightest bit of dizziness, very anorexic, and it is not a decongestant. Mentally, it is extremely benign and pleasant, funny and good-humored. No visuals. Peaceful. Easy silences, easy talking. More stoning than MDMA.

EXTENSIONS AND COMMENTARY: In general, all subjects who have explored J have accepted it and commented favorably. Perhaps those who have used supplements (in an imitation of the common MDMA procedure) achieved an additional period of effect, but also tended to drop to baseline afterwards more rapidly. The physical side effects, such as teeth clench and nystagmus, were infrequent. The consensus is that J is a bit more "stoning" than MDMA, more like MDA, but with a chronology that is very much the same.

Two nomenclature problems have to be faced in the naming of these compounds. One deals with the Chemical Abstracts terminology as contrasted with the logical and intuitive terminology. The other invokes the concept of the Muni-Metro, delightfully simple, but neither Chemical Abstracts-approved nor intuitive in form. The first problem is addressed here; the second is discussed where it better belongs, under the N-methyl homologue of J (see under METHYL-J).

In short, the two-ring system of J, or of any of the MDA-MDMA family of drugs, can be named as one ring being attached to the other, or by a single term that encompasses both. The first procedure, an old friend with chemists and the one that had been used for years in the abstracting services, calls the combination methylenedioxybenzene and, as a prefix, it becomes methylenedioxyphenyl-something. The benzene or the phenyl-something is the foundation of the name, and there happens to be a methylenedioxy-ring attached to it. On this basis, this compound J should be named as if it had no methylenedioxy ring anywhere, and then simply attach the new ring as an afterthought. So, the one-ring parent of J is 1-phenyl-2-aminobutane, and J is 1-(3,4-methylenedioxyphenyl)-2-aminobutane (or, to be a purist, the amino should alphabetically come first, to give 2-amino-1-(3,4-methylene-dioxyphenyl)butane). The synthesis of the chemical intermediates given above uses this old-fashioned nomenclature.

But the name currently in vogue for this two-ring system is 1,3-benzodioxole. As a prefix it becomes 1,3-benzodioxol-5-yl-something, and so J would be called 1-(1,3-benzodioxol-5-yl)-2-aminobutane. This is the source of the code name BDB. And the N-methyl homologue, the alpha-ethyl analogue of MDMA, is named MBDB, or METHYL-J, and is with its own separate entry in this footnote.

There is a psychological nuance to this new nomenclature. The virtues and potential medical value of MDMA lie in its most remarkable property of facilitating communication and introspective states without an overlay of psychedelic action. This property has prompted the coining of a new pharmacological class name, Entactogen, which comes from the Greek roots for "touching within." But MDMA has been badly smeared in both the public and the scientific view, by its wide popular misuse, its precipitous placement into a Schedule I category of the Federal Drug Law, and a flood of negative neurotoxicological findings in animal studies. There are some properties of both this compound and its methyl-homologue that suggest this "entactogen" world, so why not avoid the "MD" prefix that, in many eyes, is pejorative? Stick with the totally obscure chemical names, and call them BDB and MBDB. Or, even more simply, J and METHYL-J.

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