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18 Nov 2019
A major research area at the interface of chemistry and neurophysiology concerns how psychoactive compounds exert their pharmacological effects. As part of this, effort has been devoted to develop synthetic routes the provide rebuts access to families of psychoactive compounds, so that derivatives can be prepared to address basic science issues such as (i) where does the psychoactive compound bind in the brain? (ii) what types of receptors are bound? (iii) can one design synthetic analogues that provide desired behavioral effects without accompanying narcotic or addictive effects? (iv) what is the lifetime of the psychoactive compound in the nervous system, what are the metabolic products, and are such products more or less potent than the parent compound? (v) what are the differences in binding, metabolism, and resistance period upon first time exposure versus a brain that has been exposed 100 s of times in other words, what material changes does the brain undergo upon repeated exposure to psychoactive agents)? Here, citral and olivetol in dilute acid react to form tetarhydrocannabinol I (among other products); I (aka THC) is the stereochemistry impure form of the chief physiologically active constituent of cannabis. This reaction provides an example of how molecules of some degree of architectural complexity can form spontaneously from simple ingredients under simple conditions. i) Propose a mechanism for the acid catalyzed reaction of citral and olivetol to form I. ii) How many stereoisomers are there of I? iii) Propose a synthetic of olivetol beginning with benzene and pentatonic acid. For a few of the next problems, note that LiAIH_4 is a more potent version of NaBH_4. Thus, RCHO + LiAIH_4 rightarrow RCH_2OH(NaBH_4 affords the same reaction) R_2C=O + LiAIH_4 rightarrow R_2CHOH (NaBH_4 affords the same reaction) RCH_2-OT_s + LiAIH_4 rightarrow RCH_3(NaBH_4 lacks the potency to do this S_N 2 reaction) Predict the products.
A major research area at the interface of chemistry and neurophysiology concerns how psychoactive compounds exert their pharmacological effects. As part of this, effort has been devoted to develop synthetic routes the provide rebuts access to families of psychoactive compounds, so that derivatives can be prepared to address basic science issues such as (i) where does the psychoactive compound bind in the brain? (ii) what types of receptors are bound? (iii) can one design synthetic analogues that provide desired behavioral effects without accompanying narcotic or addictive effects? (iv) what is the lifetime of the psychoactive compound in the nervous system, what are the metabolic products, and are such products more or less potent than the parent compound? (v) what are the differences in binding, metabolism, and resistance period upon first time exposure versus a brain that has been exposed 100 s of times in other words, what material changes does the brain undergo upon repeated exposure to psychoactive agents)? Here, citral and olivetol in dilute acid react to form tetarhydrocannabinol I (among other products); I (aka THC) is the stereochemistry impure form of the chief physiologically active constituent of cannabis. This reaction provides an example of how molecules of some degree of architectural complexity can form spontaneously from simple ingredients under simple conditions. i) Propose a mechanism for the acid catalyzed reaction of citral and olivetol to form I. ii) How many stereoisomers are there of I? iii) Propose a synthetic of olivetol beginning with benzene and pentatonic acid. For a few of the next problems, note that LiAIH_4 is a more potent version of NaBH_4. Thus, RCHO + LiAIH_4 rightarrow RCH_2OH(NaBH_4 affords the same reaction) R_2C=O + LiAIH_4 rightarrow R_2CHOH (NaBH_4 affords the same reaction) RCH_2-OT_s + LiAIH_4 rightarrow RCH_3(NaBH_4 lacks the potency to do this S_N 2 reaction) Predict the products.
Jamar FerryLv2
3 Jun 2019