Sudafed alternative for ephedra?

February 24, 2009

, " Michael Tierra "

<mtierra wrote:

>

> Question? I don't believe there is a substitute for ephedra and I

wondered

> why one might not prescribe a dose of Sudafed (pseudoephedrine)

along with

> formulas the indicate the use of ephedra? It seems the closest

chemically

> and in terms of its clinical effects and uses to ephedra.

However, the principle constituent of ma huang (ephedra) is ephedrine,

not pseudoephedrine. These two compounds naturally occur in ma huang,

but Chinese ma huang contains much more ephedrine than

pseudoephedrine. In terms of pharmacology, most of the effects of ma

huang pertain to ephedrine rather than pseudoephedrine.

Despite the fact that ephedrine and pseudoephedrine are very closely

related chemically (they are optical isomers of the same basic

compound), they are quite different in terms of their pharmacology.

In the case of ephedrine vs. pseudoephedrine, pseudoephedrine lacks

the CNS stimulating effects yet retains decongestant effects. This

makes sudafed a desirable medication but it is hard to say that it

could be thought of as equivalent to ephedrine.

Many drugs only have medical utility in one of their optical isomers,

typically if the " left-handed " isomer is active, the " right-handed "

isomer is inactive, and vice versa. Pseudoephedrine and ephedrine are

exceptions because both isomers have activity, although their actions

are quite different. But drugs with only one desirable isomer abound,

L-dopa is a classic example where only one isomer is used. And I

believe the famous issue of birth defects from thalidomide arose

because two optical isomers were mixed together when only one should

have been used. There are many examples in medicine where this

optical isomer switch makes all the difference in the world, I'd be

hesitant to support the idea that only one isomer (esp. the minor one)

would be able to be an effective substitute for ma huang, which

contains both. Maybe if we were only using ma huang as a

decongestant, that would be ok, but we use it for many other purposes.

In fact, many stimulant drugs are useful for asthma, so it is likely

that part of ma huang's ability to treat panting could be related more

closely to its ephedrine content than its comparatively low

pseudoephedrine content.

By all means, I like your thinking and I'm sure that many great

discoveries could come out of this type of integrative, applied logic.

Since you are soliciting opinions, I'm sharing mine, but please

understand that I really like your question and I value your thoughts

on the issue. Nobody really knows the answer to this question, and we

will never discover new things without thinking outside the box like

you are doing.

Incidentally, in California it is almost easier to get ma huang than

it is to get sudafed, what with the whole meth craze and all.

Mormon tea might be a suitable substitute for sudafed, as it lacks

ephedrine but contains pseudoephedrine.

Eric

February 24, 2009

Eric,

Do you have a reference for Ephedra nevadensis containing

pseudoephedrine? I haven't seen that in the literature. In fact, E.

nevadensis has been used as a negative control in studies looking for

ephedrine alkaloids in the Chinese Ephedra species.

A couple of comments on pseudoephedrine. In some species, such as E.

intermedia and E. lomatolepis, some samples actually show higher

levels of pseudoephedrine than ephedrine. Most species do contain more

ephedrine than pseudoephedrine, but the pseudoephedrine content is

still significant. Samples of E. sinica have tested at 75 - 85%

ephedrine and 15 - 25% pseudoephedrine.

Regarding the lack of cardiac effects with pseudoephedrine, it is

definitely less than ephedrine but is still a possibility. There have

been adverse events with high doses of pseudoephedrine, but low dose

studies rarely show cardiac effects.

- Bill

, " Eric Brand "

<smilinglotus wrote:

>

> , " Michael Tierra "

> <mtierra@> wrote:

> >

> > Question? I don't believe there is a substitute for ephedra and I

> wondered

> > why one might not prescribe a dose of Sudafed (pseudoephedrine)

> along with

> > formulas the indicate the use of ephedra? It seems the closest

> chemically

> > and in terms of its clinical effects and uses to ephedra.

>

> However, the principle constituent of ma huang (ephedra) is ephedrine,

> not pseudoephedrine. These two compounds naturally occur in ma huang,

> but Chinese ma huang contains much more ephedrine than

> pseudoephedrine. In terms of pharmacology, most of the effects of ma

> huang pertain to ephedrine rather than pseudoephedrine.

>

> Despite the fact that ephedrine and pseudoephedrine are very closely

> related chemically (they are optical isomers of the same basic

> compound), they are quite different in terms of their pharmacology.

> In the case of ephedrine vs. pseudoephedrine, pseudoephedrine lacks

> the CNS stimulating effects yet retains decongestant effects. This

> makes sudafed a desirable medication but it is hard to say that it

> could be thought of as equivalent to ephedrine.

>

> Many drugs only have medical utility in one of their optical isomers,

> typically if the " left-handed " isomer is active, the " right-handed "

> isomer is inactive, and vice versa. Pseudoephedrine and ephedrine are

> exceptions because both isomers have activity, although their actions

> are quite different. But drugs with only one desirable isomer abound,

> L-dopa is a classic example where only one isomer is used. And I

> believe the famous issue of birth defects from thalidomide arose

> because two optical isomers were mixed together when only one should

> have been used. There are many examples in medicine where this

> optical isomer switch makes all the difference in the world, I'd be

> hesitant to support the idea that only one isomer (esp. the minor one)

> would be able to be an effective substitute for ma huang, which

> contains both. Maybe if we were only using ma huang as a

> decongestant, that would be ok, but we use it for many other purposes.

> In fact, many stimulant drugs are useful for asthma, so it is likely

> that part of ma huang's ability to treat panting could be related more

> closely to its ephedrine content than its comparatively low

> pseudoephedrine content.

>

> By all means, I like your thinking and I'm sure that many great

> discoveries could come out of this type of integrative, applied logic.

> Since you are soliciting opinions, I'm sharing mine, but please

> understand that I really like your question and I value your thoughts

> on the issue. Nobody really knows the answer to this question, and we

> will never discover new things without thinking outside the box like

> you are doing.

>

> Incidentally, in California it is almost easier to get ma huang than

> it is to get sudafed, what with the whole meth craze and all.

> Mormon tea might be a suitable substitute for sudafed, as it lacks

> ephedrine but contains pseudoephedrine.

>

> Eric

>

February 25, 2009

Eric,

I would also like to see that reference.....I have looked and to the

best of my knowledge, research (that plant is in my book and I have

used it quite a bit clinically) there is neither ephedrine nor

psuedoephedrine.

Thomas

> Eric,

>

> Do you have a reference for Ephedra nevadensis containing

> pseudoephedrine? I haven't seen that in the literature. In fact, E.

> nevadensis has been used as a negative control in studies looking for

> ephedrine alkaloids in the Chinese Ephedra species.

>

February 25, 2009

, " bill_schoenbart "

<plantmed2 wrote:

>

> Eric,

>

> Do you have a reference for Ephedra nevadensis containing

> pseudoephedrine? I haven't seen that in the literature. In fact, E.

> nevadensis has been used as a negative control in studies looking for

> ephedrine alkaloids in the Chinese Ephedra species.

>

> A couple of comments on pseudoephedrine. In some species, such as E.

> intermedia and E. lomatolepis, some samples actually show higher

> levels of pseudoephedrine than ephedrine. Most species do contain more

> ephedrine than pseudoephedrine, but the pseudoephedrine content is

> still significant. Samples of E. sinica have tested at 75 - 85%

> ephedrine and 15 - 25% pseudoephedrine.

Thank you for the corrections Bill. I know very little about Western

herbs in comparison to Michael Tierra and yourself, but I'd like to

learn more. I don't know where I had heard the Western

ephedra/pseudoephedrine thing, but it is clear that I was mistaken.

I've since looked into it on pubmed, and you are absolutely correct

that it Ephedra nevadensis has been used as a negative control and

appears to be totally lacking in alkaloids.

This is interesting because it illustrates the fact that similar

plants in different environments often have dramatically different

chemical profiles (and corresponding clinical effects). Also

interesting is that several Chinese species also lack significant

alkaloid content, and are likewise considered to be inappropriate

substitutes for ma huang.

You are also correct with regard to the different alkaloid profiles of

the three official ephedra species used in Chinese medicine. I am

under the impression that Ephedra sinica is the most prominent one on

the market (didn't realize its PE content was so significant, though).

However, I wonder what the relative prevalence of the different

Chinese ephedra species is on the market. For example, I saw a pubmed

article from Taiwan that assessed samples of multiple different

ephedra species from the marketplace, so clearly all three official

species can be found on the market. I happen to be in Hong Kong right

now, and Prof. Zhao Zhongzhen here should be able to give us an answer

to this question when I see him this afternoon, I'll post the info to

the group.

Anyway, thank you very much for correcting my mistake. I had never

looked into the issue in detail before, and I've learned a lot in the

process. Another interesting thing I noticed in the scientific

literature was that the alkaloid content is higher in the nodes. This

is interesting because the nodes were removed in ma huang tang but

left intact in san ao tang. Thousands of years before HPLC, they

clearly knew that there was something about the nodes, fascinating.

When chatting with Dr. Zhao the other day, I also learned something

interesting about gou qi zi. I knew that it should have a more

purplish color instead of a more bright red color. However, I did not

know that the shape and hardness are important. Apparently, gou qi zi

should be long and pointy instead of round, and should be hard instead

of soft. These features can be used to distinguish the xinjiang-grown

product from the ningxia-grown product (ningxia is superior). Dr.

Zhao said that the hard ones are much richer in polysaccharides than

the soft ones. I thought that was interesting because I had always

assumed that softer meant fresher and better, but apparently that is

not so.

Eric Brand

February 26, 2009

, " Eric Brand "

<smilinglotus wrote:

> You are also correct with regard to the different alkaloid profiles of

> the three official ephedra species used in Chinese medicine. I am

> under the impression that Ephedra sinica is the most prominent one on

> the market (didn't realize its PE content was so significant, though).

> However, I wonder what the relative prevalence of the different

> Chinese ephedra species is on the market.

According to Dr. Zhao Zhongzhen, one of the world's top experts in

pharmacy, Ephedra sinica accounts for about 70% of the ma huang on the

Hong Kong market. This species is regarded as the best, so it is the

most commonly cultivated variety at present. (This species is the one

with the high proportion of ephedrine and a comparatively low

proportion of pseudoephedrine).

Eric

February 27, 2009

There have been people in the past who have claimed to find ephedrine

alkaloids in Mormon tea, so the confusion is understandable.

, " Eric Brand "

<smilinglotus wrote:

>

> , " bill_schoenbart "

> <plantmed2@> wrote:

> >

> > Eric,

> >

> > Do you have a reference for Ephedra nevadensis containing

> > pseudoephedrine? I haven't seen that in the literature. In fact, E.

> > nevadensis has been used as a negative control in studies looking for

> > ephedrine alkaloids in the Chinese Ephedra species.

> >

> > A couple of comments on pseudoephedrine. In some species, such as E.

> > intermedia and E. lomatolepis, some samples actually show higher

> > levels of pseudoephedrine than ephedrine. Most species do contain more

> > ephedrine than pseudoephedrine, but the pseudoephedrine content is

> > still significant. Samples of E. sinica have tested at 75 - 85%

> > ephedrine and 15 - 25% pseudoephedrine.

>

> Thank you for the corrections Bill. I know very little about Western

> herbs in comparison to Michael Tierra and yourself, but I'd like to

> learn more. I don't know where I had heard the Western

> ephedra/pseudoephedrine thing, but it is clear that I was mistaken.

> I've since looked into it on pubmed, and you are absolutely correct

> that it Ephedra nevadensis has been used as a negative control and

> appears to be totally lacking in alkaloids.

>

> This is interesting because it illustrates the fact that similar

> plants in different environments often have dramatically different

> chemical profiles (and corresponding clinical effects). Also

> interesting is that several Chinese species also lack significant

> alkaloid content, and are likewise considered to be inappropriate

> substitutes for ma huang.

>

> You are also correct with regard to the different alkaloid profiles of

> the three official ephedra species used in Chinese medicine. I am

> under the impression that Ephedra sinica is the most prominent one on

> the market (didn't realize its PE content was so significant, though).

> However, I wonder what the relative prevalence of the different

> Chinese ephedra species is on the market. For example, I saw a pubmed

> article from Taiwan that assessed samples of multiple different

> ephedra species from the marketplace, so clearly all three official

> species can be found on the market. I happen to be in Hong Kong right

> now, and Prof. Zhao Zhongzhen here should be able to give us an answer

> to this question when I see him this afternoon, I'll post the info to

> the group.

>

> Anyway, thank you very much for correcting my mistake. I had never

> looked into the issue in detail before, and I've learned a lot in the

> process. Another interesting thing I noticed in the scientific

> literature was that the alkaloid content is higher in the nodes. This

> is interesting because the nodes were removed in ma huang tang but

> left intact in san ao tang. Thousands of years before HPLC, they

> clearly knew that there was something about the nodes, fascinating.

>

> When chatting with Dr. Zhao the other day, I also learned something

> interesting about gou qi zi. I knew that it should have a more

> purplish color instead of a more bright red color. However, I did not

> know that the shape and hardness are important. Apparently, gou qi zi

> should be long and pointy instead of round, and should be hard instead

> of soft. These features can be used to distinguish the xinjiang-grown

> product from the ningxia-grown product (ningxia is superior). Dr.

> Zhao said that the hard ones are much richer in polysaccharides than

> the soft ones. I thought that was interesting because I had always

> assumed that softer meant fresher and better, but apparently that is

> not so.

>

> Eric Brand

>

February 27, 2009

I'd like to testify that Ephedra nevadensis has some stimulant properties

regardless of its constituents. If you chance upon some chew it up and see for

yourself. This has been the consensus amongst many people I've talked to and

engaged in such participatory education with.

I've also heard second hand, and am curious as to what an ethnobotanical lit.

review might turn up, that the native groups on the Eastern slope of the Sierra

Nevada, where the plant is prevelant used to, and continue to use E. nevadensis