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| Clinical data | |
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| Other names | 2C-D-DEMPDHPCA; "Compound 45"[1] |
| Drug class | Possibleserotonergic psychedelic orhallucinogen |
| ATC code |
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| Identifiers | |
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| Chemical and physical data | |
| Formula | C20H30N2O3 |
| Molar mass | 346.471 g·mol−1 |
| 3D model (JSmol) | |
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DEMPDHPCA-2C-D is a possibleserotonergic psychedelic of thephenethylamine and2C families.[1] It is acyclized phenethylamine and apartial or simplified lysergamide.[1] More specifically, the compound is aderivative of2C-D in which the β position has beencyclized with theamine to form atetrahydropyridinering that is substituted such that it is identical to the D ring ofLSD.[1] Alternatively, it may be viewed as ananalogue of LSD in which the B and C rings have been removed and 4-methyl and 2,5-dimethoxy substitutions have been added to the phenyl ring (i.e., the A ring of LSD).[1]
Thesynthesis of DEMPDHPCA-2C-D was attempted byDavid E. Nichols in hisPhDthesis in 1973, though it was not successful.[1] However, several close analogues of DEMPDHPCA-2C-D, such asDEMPDHPCA and a few of its derivatives, have been reported to bepotentserotonin5-HT2A receptoragonists[2] or to producehallucinogen-like behavioral effects in animals.[3] In addition, the established putative psychedelicLPH-5 ((S)-2C-TFM-3PIP) is similar to DEMPDHPCA-2C-D inchemical structure but most notably lacks the LSD-likeN,N-diethylamide andolefinmoieties.[4][5]
Part III. Proposed Synthesis of an LSD AD-Ring Congener To study the importance of the D ring of LSD it was proposed to prepare 45. This system presumably would possess a high HOMO as conferred on the system by the 2,5- dimethoxy-4-methyl substitution and is a close analog of LSD. [...]
The gross behavior of the test animals under the influence of 160a-d was observed during the course of the dose-response study depicted by Figure 7. The gross behavioral signs displayed by rats under the influence of the phenyl (160a) and trimethoxyphenyl (160c) homologs were indistinguishable from those exhibited with LSD, DMT or mescaline, and were characterized by general inactivity, muscle twitching and the occurrence of a Straub tail reaction (a somewhat specific indication of the influence of a psychotomimetic drug in which the tail is held in an upright 191 position ). The naphthyl homolog (160d) produced similar behavioral signs but the rats were more active than with 160a and 160c. The gross behavioral pattern of rats under the influence of the methoxy homolog (160b), in contrast, was not at all similar to that caused by LSD, 160a or 160c. It more closely resembled the pattern exhibited with amphetamine, characterized by very marked hyperactivity. [...] Initial indications, based on the gross behavioral comparisons mentioned previously, are that 160a,c,d possess psychotomimetic activity similar to LSD, while 160b possesses amphetamine-like stimulatory activity. [...] On the other hand, 160a, whose structure more closely resembles that of LSD, seems to have LSD-like activity of greater potency than either 160b or 160c. Since the structure of 160a is very closely related to the structure of LSD and contains no aryl methoxy groups necessary for psychotomimetic activity in the methoxyamphetamine series, it could be inferred that 160a acts via an LSD-like mechanism. [...] SUMMARY [...]
