Methamphetamine derivs

Synthesis. The synthesis of the amphetamine and methamphetamine derivatives in the benzobicyclo[2.2.2]-octene system has been described elsewhere (141 and references cited therein). To be able to study certain of the pharmacological aspects of these compounds, 3H-derivatives were prepared of NM-X and NM-N by reducing the N-formyl derivatives of the amphetamine analogs NH-X and NH-N with lithium aluminum tritiide (142). 

Amphetamine and methamphetamine, PEA derivatives with a long lasting effect, share with their parent compound the releasing property. (-)-Deprenyl was the first PEA/methamphetamine derivative that maintained the enhancer... 

Methamphetamine (derivative of amphetamine) is increasingly used on the west... 

S Inayama, Y Tokunaga, E Hosoya, T Nakadate, T Niwaguchi, K Aoki, S Saito. A rapid and simple screening method for methamphetamine in urine by radioimmunoassay using a 1251-labeled methamphetamine derivative. Chem Pharm Bull (Tokyo) 28 2779, 1980. 

Methamphetamine, derived from ephedrine, and cocaine [1], and caffeine are known as CNS stimulants, though the strength of each activity is different. On the other hand, strychnine isolated from the seed of Strychnos nux-vomica (Loganiaceae) stimulates the reflex function of the spinal cord. That is to say, it is a stimulant of the spinal cord in the CNS. 

The drugs 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methyl-enedioxyamphetamine (MDA) are ring-substituted derivatives of methamphetamine and amphetamine, respectively. These methylenedioxy-substituted amphetamines have been reported to exhibit both stimulant and psychotomimetic properties (Anderson et al. 1978 Braun et al. 1980 ... 

As shown in table 6, we have compared the affinities of a series of methylenedioxy derivatives with those of the parent compounds (amphetamine and methamphetamine) at some of the recognition sites in brain at which MDMA exhibited the highest affinities. These comparative studies indicate that addition of the methylenedioxy subshtuent in the 3,4 position inereases their affinity at serotonin uptake, 5-HT2 serotonin, and M-1 muscarinic receptors, while the unsubstituted parent compounds appear to be more potent at Ct2-iadrenergic receptors. 

McMillan, D.E., Hardwick, W.C., Li, M. et al. Effects of murine-derived anti-methamphetamine monoclonal antibodies on (+)-methamphetamine self-administration in the rat. J. Pharmacol. Exp. Ther. 309 1248, 2004. 

Banta-Green CJ, Field JA, Chiaia AC, Sudakin DL, Power L, De Montigny L (2009) The spatial epidemiology of cocaine, methamphetamine and 3, 4-methylenedioxymethamphetamine (MDMA) use a demonstration using a population measure of community drug load derived from municipal wastewater. Addiction 104 1874—1880... 

N-substituted mescaline derivatives and methamphetamine analogs Diss. Abst. Int. 32B,5704,5706(1972). 

When using PFT with a neutral selector, it is quite difficult to avoid any entrance of the chiral selector into the ionization source, particularly at a high pH, where EOF is important. The use of BGE at low pH and/or coated capillary to minimize EOF is therefore mandatory. However, the coaxial sheath gas, which generally assists the ionization process, leads to an aspirating phenomenon of the chiral selector in the MS direction. Javerfalk et al. were the first to apply PFT with a neutral methyl-/i-CD for the separation of racemic bupivacaine and ropivacaine with a polyacrylamide-coated capillary and an acidic pH buffer (pH 3). Cherkaoui et al. employed another neutral CD (HP-/1-CD) with a PVA-coated capillary for the analysis of amphetamines and their derivatives. To prevent a detrimental aspiration effect, analyses were carried out without nebulization pressure. Numerous other studies presented excellent results such as the enantioselective separation of adrenoreceptor antagonist drugs using tandem mass spectrometry (MS/MS) the separation of clenbuterol enantiomers after solid-phase extraction (SPE) of plasma samples or the use of CD dual system for the simultaneous chiral determination of amphetamine, methamphetamine, dimethamphetamine, and p-hydroxymethamphetamine in urine. 

FIGURE 4 Chiral CE ESI/MS analysis of five amphetamine derivatives and two pharmaceutical compounds. Total ion current (TIC) and extracted ion currents (XIC) of amphetamine (A), methamphetamine (MA), methylenedioxyamphetamine (MDA), methylenedioxymethamphetamine (MDMA), and methylenedioxyethylamphetamine (MDEA), and tramadol (TMD) and methadone (MTD) in plasma after LLE with electrokinetic injection. 

Phenyl-2-propanone Used in the chemical and pharmaceutical industries for the manufacture of amphetamine, methamphetamine and some derivatives used for the synthesis of propylhexedrine. 

In addition Choi et al. utilized FlTC-labeled methamphetamine for competitive immunoassay of methamphetamine in urine (19). Instead of purified antibody or antibody fragment, antiserum was used. An aminobutyl derivative of metamphetamine was conjugated with proteins and used as an immunogen to produce antibodies for the assay. The free FITC-labeled tracer was well separated from the antibody-bound fraction, and the detection limit for the CE assay was lower than that for ELISA. 

A further, indirect indication of methamphetamine production can be derived from the geographical location of ephedrine and pseudo-ephedrine seizures. The largest such seizures in Asia over the 2004-2005 period were reported from China (which is also one of the main licit producers of ephedrine and pseudo-ephedrine), followed by the Philippines, Myanmar, Indonesia and India (another major licit producer of ephedrine and pseudo-ephedrine), and at far lower levels, Hong Kong SAR of China and Thailand. Taken together, the Asian countries accounted for 89 per cent of the world s ephedrine and pseudo-ephedrine seizures in 2005.20... 

Cimbura and Kofoed (50),mentioned earlier, used GLC to separate amphetamine and methamphetamine after acetylation with acetic anhydride in methanol. Derivatives were extracted using diethyl ether and chromatographed op columns of either 3% OV-17, OV-1, or SE-30. Column temperature was 160°C. They also reported the chromatographic determination of acetylated morphine on 3% SE-30, OV-1, or OV-17 at temperatures of 220°C. Cruickshank et al.(21) separated 21 amino acids as their trifluoroacetylated methyl esters. The column was 5% neopentyl glycol succinate on Gas Chrom P. Column temperatures were both isothermal and programmed 65°C for 20 min at 1.5°C/min then 2°C/min until 42.5 min then 4°C/min until 60 min then isothermal until about 75 min (see Figure 12.2). Chang et al. (19), used BSA/pyridine to form the TMS derivatives of levodopa, methyldopa, tyrosine. 

D-Methamphetamine, the AZ-methyl derivative of amphetamine, was first synthesized in 1919. Methamphetamine is available in the d- and l-forms. The D-form has reportedly greater central stimulant activity than the L-isomer, which has greater peripheral sympathomimetic activity. The D-form is the commonly abused form while the L-isomer is typically found in nonprescription inhalers as a decongestant. 

FIGURE 13—6. Icon of amphetamine/methamphetamine. Amphetamine (principally -amphetamine) and related derivatives such as methamphetamine are also releasers of dopamine, with a mechanism similar to that described for cocaine. 

Several people have asked me what I thought about the potential activity of a compound with a methyl group added to DMMDA. One of these possibilities would be the N-methylated derivative, 2,5-dimethoxy-N-methyl-3,4-methylene-dioxyamphetamine, or METHYL-DMMDA (or DMMDMA for the dimethoxy-methylenedioxy-methamphetamine nomenclature). It is a MDMA analogue, and is described in the recipe for METHYL-MMDA-2. 

Moreover, nitrones can be generated from N-hydroxy products during extraction into an organic solvent, such as diethyl ether. The latter contains acetaldehyde as an impurity even after careful distillation. Indeed, nitrones arising as artifacts from the reaction of primary hydroxylamines, metabolically derived from methamphetamine and chlorpromazine, with acetaldehyde upon sample treatment with ether have been identified23,39. Acetone is frequently used as one of the components of the solvent systems applied for TLC analysis. 

McCooeye, M. A., Mester, Z., Ells, B., Barnett, D. A., Purves, R. W., and Guevremont, R. (2002). Quantitation of amphetamine, methamphetamine, and their methylenedioxy derivatives in urine by solid-phase microextraction coupled with electrospray ionization-high-field asymmetric waveform ion mobility spectrometry-mass spectrometry. Anal. Chem. 74 3071-3075. 

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